JPS5831330B2 - 1-hexadecin-6-one - Google Patents

1-hexadecin-6-one

Info

Publication number
JPS5831330B2
JPS5831330B2 JP6915976A JP6915976A JPS5831330B2 JP S5831330 B2 JPS5831330 B2 JP S5831330B2 JP 6915976 A JP6915976 A JP 6915976A JP 6915976 A JP6915976 A JP 6915976A JP S5831330 B2 JPS5831330 B2 JP S5831330B2
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JP
Japan
Prior art keywords
compound
formula
reaction
acid
yield
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
JP6915976A
Other languages
Japanese (ja)
Other versions
JPS52153906A (en
Inventor
正直 松井
謙治 森
稔 内多
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Otsuka Pharmaceutical Co Ltd
Original Assignee
Otsuka Pharmaceutical Co Ltd
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Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd
Priority to JP6915976A priority Critical patent/JPS5831330B2/en
Publication of JPS52153906A publication Critical patent/JPS52153906A/en
Publication of JPS5831330B2 publication Critical patent/JPS5831330B2/en
Expired legal-status Critical Current

Links

Description

【発明の詳細な説明】 本発明は新規化合物l−ヘキサデシン−6−オンに関す
る。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel compound l-hexadecyn-6-one.

本発明の化合物はオリギア シュード ツガータ(マツ
クダナーフ) (Orgia pseudotsug
ata(McDunnough ) )の性ホルモンシ
ス−6−ヘンアイラセン−11−オンの合成中間体とし
て有用な化合物である。
The compounds of the present invention can be applied to Orgia pseudotsugata (Orgia pseudotsugata).
This compound is useful as an intermediate for the synthesis of the sex hormone cis-6-henairasen-11-one produced by A.ta (McDunnough).

従来シス−6−ヘンアイラセン−11−オンの合成はス
ミス等(R,G、Sm1th and G、D。
Conventional synthesis of cis-6-henairasen-11-one was performed by Smith et al.

Daves Jr )により報告されている(J、O
rg。
Daves Jr.) (J, O
rg.

Chem、、 40,1593(1975))。Chem, 40, 1593 (1975)).

この方法はC1oH21CHOからシス−6−ヘンアイ
ラセン−11−オンを誘導する方法であるが、この方法
には(a)出発原料の化合物が容易に入手できないこと
、(b)試薬として悪臭の強いトリメチレンチオグリコ
ール及び酸化クロム、酸化銅、ニッケル等有毒性重金属
を使用しているために環境汚染のおそれがあること、(
c)上記試薬を完全に回収しなければならず製造コスト
が必然的に高くなること等の欠点があり工業化に難点が
ある。
This method is a method for deriving cis-6-henairasen-11-one from C1oH21CHO, but this method has two drawbacks: (a) the starting material compound is not easily available, and (b) trimethylene, which has a strong odor, is used as a reagent. There is a risk of environmental pollution due to the use of thioglycol and toxic heavy metals such as chromium oxide, copper oxide, and nickel.
c) There are drawbacks such as the need to completely recover the reagent, which inevitably increases production costs, and this poses difficulties in industrialization.

しかるに本発明化合物を出発原料として用いると上記の
如きトリメチレンチオグリコール及び有毒性重金属を使
用することなく、従って上記(a)、(b)、及び(e
)の欠点を全て解消してシス−6−ヘンアイコセン11
−オンを製造し得る。
However, when the compound of the present invention is used as a starting material, the above-mentioned trimethylenethioglycol and toxic heavy metals are not used, and therefore the above-mentioned (a), (b), and (e) can be obtained.
) by eliminating all the drawbacks of cis-6-heneicosene 11
- can be produced.

本発明の化合物l−ヘキサデシン−6−オンは本発明者
が初めて見い出した新規化合物であり、例えば容易に入
手可能な公知のジヒドロレゾルシノールを出発原料とし
て下式の如くして製造される。
The compound 1-hexadecyn-6-one of the present invention is a novel compound discovered for the first time by the present inventor, and can be produced, for example, by the following formula using easily available known dihydroresorcinol as a starting material.

式(II)の化合物は公知の方法COrg、 Syn。Compounds of formula (II) can be prepared by known methods COrg, Syn.

Co110.5.539〕を適用することにより即ち例
工ばp−4ルエンスルホン酸の存在下ジヒドロレゾルシ
ノール〔■〕にエタノールを反応させることにより容易
に得られる。
Co110.5.539], for example, by reacting dihydroresorcinol [■] with ethanol in the presence of p-4 luenesulfonic acid.

次いで得られる式〔川〕の化合物と一般式n −C1o
H21X (式中Xは)・ロゲン原子)で表わされる
ハロゲン化物とをリチウム、ナトリウム、カリウム等の
アルカリ金属の存在下エーテル、ジオキサン、テトラヒ
ドロフラン、n−ヘキサン、シクロヘキサン等の不活性
溶媒中で反応させて式〔■〕の化合物とし、式〔■〕の
化合物を単離することなく塩酸、硫酸等の通常の酸で加
水分解することにより新規な式(IV)の化合物が得ら
れる。
Then, the compound of the formula [river] and the general formula n -C1o
A halide represented by H21X (in the formula, A novel compound of formula (IV) can be obtained by hydrolyzing the compound of formula [■] with a common acid such as hydrochloric acid or sulfuric acid without isolating the compound of formula [■].

これらの反応に於てアルカリ金属の使用量は式(II)
の化合物1モルに対して通常等モル〜犬過剰量、好まし
くは3〜5倍モルであり、またハロゲン化物の使用量は
式〔川〕の化合物1モルに対して通常等モル〜犬過剰量
、好ましくは等モル−1,2倍モルである。
The amount of alkali metal used in these reactions is expressed by formula (II)
The amount of the halide used is usually an equimole to an excess amount, preferably 3 to 5 times the mole of the compound, and the amount of the halide used is usually an equimole to an excess amount per mole of the compound of the formula [river]. , preferably equimolar to 1 to 2 times the molar amount.

これらの反応は室温下、冷却下あるいは加温下で行なう
ことができ通常−78℃〜40℃、好ましくは室温で行
なわれ、反応時間は1〜5時間程度である。
These reactions can be carried out at room temperature, cooling or heating, and are usually carried out at -78°C to 40°C, preferably at room temperature, and the reaction time is about 1 to 5 hours.

式(IV)の化合物を水、メタノール、エタノール塩化
メチレン、四塩化炭素等の溶媒中でエポキシ化反応させ
ることにより新規な式(V)の化合物が得られる。
A novel compound of formula (V) can be obtained by subjecting the compound of formula (IV) to an epoxidation reaction in a solvent such as water, methanol, ethanol, methylene chloride, or carbon tetrachloride.

このエポキシ化反応に使用されろ過酸としては公知のも
のを広く使用でき、例えばメタクロル過安息香酸、過酢
酸、過酸化水素等を例示できる。
As the filter acid used in this epoxidation reaction, a wide variety of known filter acids can be used, such as methachloroperbenzoic acid, peracetic acid, hydrogen peroxide, and the like.

あるL・は上記過酸と共に水酸化ナトリウム若しくは水
酸化カリウムを使用してもよい。
For certain L., sodium hydroxide or potassium hydroxide may be used together with the above peracid.

これらのアルカリを用いる場合には過酸化水素のナトリ
ウム塩、過酸化水素のカリウム塩、t−ブチルヒドロパ
ーオキシドのナトリウム塩、t−ブチルヒドロパーオキ
シドのカリウム塩等に予め調製しておくのが望ましい。
When using these alkalis, it is recommended to prepare them in advance as sodium salt of hydrogen peroxide, potassium salt of hydrogen peroxide, sodium salt of t-butyl hydroperoxide, potassium salt of t-butyl hydroperoxide, etc. desirable.

本発明に於てはこれらの中でも過酸化水素のす) IJ
ウム塩若しくはカリウム塩、t−ブチルヒドロパーオキ
シドのナトリウム塩若しくはカリウム塩を用L・るのが
特に好ましい。
In the present invention, among these, hydrogen peroxide is used) IJ
Particularly preferred is the sodium or potassium salt of tert-butyl hydroperoxide.

該反応に使用されろ過酸及びアルカリの使用量は式(I
V)の化合物1モルに対I7てそれぞれ等モル−犬過剰
量(好ましくは3〜5倍モル)、03〜2倍モル(好ま
しくは0.5倍モル)である。
The amounts of filtered acid and alkali used in the reaction are determined by the formula (I
The amount of I7 per mole of compound V) is equimolar excess (preferably 3 to 5 times the mole) and 03 to 2 times the mole (preferably 0.5 times the mole).

該反応は常温であるいは冷却下で行なわれ通常20〜3
0℃、好ましくは20〜25℃であり反応時間は通常1
〜6時間である。
The reaction is carried out at room temperature or under cooling, and is usually 20 to 3
The temperature is 0°C, preferably 20-25°C, and the reaction time is usually 1
~6 hours.

上記で得られる式〔■〕の化合物につきエツシエンモー
ゼル(Eschenmoser )開裂反応させること
により本発明化合物(式(Vl)の化合物)が得られる
The compound of the present invention (compound of formula (Vl)) is obtained by subjecting the compound of formula [■] obtained above to Eschenmoser cleavage reaction.

エツシエンモーゼル開裂反応とは、α・β−エポキシケ
トンを開裂反応させて分子内にカルボニル基と三重結合
とを導入する反応である(J。
The Etsien-Mosel cleavage reaction is a reaction in which a carbonyl group and a triple bond are introduced into the molecule by cleavage of α/β-epoxyketone (J.

Ory、 Chem、、40 (5)、57.9(19
75)参照〕。
Ory, Chem, 40 (5), 57.9 (19
75)].

本反応によれば、以下に詳細に説明しているように、適
当な触媒の存在下溶媒中にて式(V)の化合物を処理す
ることにより本発明化合物が製造される。
According to this reaction, as explained in detail below, the compound of the present invention is produced by treating the compound of formula (V) in a solvent in the presence of an appropriate catalyst.

該反応に用いられる触媒としてはpトルエンスルホニル
ヒドラジド、p−ニトロフェニルスルホニルヒドラジド
、フェニルスルホニルヒドラジド等のアリールスルホニ
ルヒドラジド、エチルスルホニルヒドラジド等の低級ア
ルキルスルホニルヒドラジド等を例示できるが、この中
でもアリールスルホニルヒドラジドを用いるのが好まし
い。
Examples of catalysts used in this reaction include arylsulfonyl hydrazides such as p-toluenesulfonyl hydrazide, p-nitrophenylsulfonyl hydrazide, and phenylsulfonyl hydrazide, and lower alkylsulfonyl hydrazides such as ethylsulfonyl hydrazide. It is preferable to use

該反応で使用される溶媒としては塩化メチレン、クロロ
ホルム 1・2−ジクロロエタン、酢酸、蟻酸、エーテ
ル、ジオキサン、ジメチルホルムアミド、・ジメチルス
ルホキシド等を例示できる。
Examples of the solvent used in the reaction include methylene chloride, chloroform, 1,2-dichloroethane, acetic acid, formic acid, ether, dioxane, dimethylformamide, and dimethylsulfoxide.

本発明では塩化メチレン−酢酸あるいはクロロホルム−
酢酸の混合溶媒を用いるのが好ましい。
In the present invention, methylene chloride-acetic acid or chloroform-
Preferably, a mixed solvent of acetic acid is used.

該反応で使用される触媒の使用量は特に限定されないが
式〔■〕の化合物1モルに対して通常05〜※※1.5
倍モル、好ましくは等モル程度である。
The amount of the catalyst used in the reaction is not particularly limited, but is usually 05 to ※※1.5 per mol of the compound of formula [■].
The amount is twice the molar amount, preferably about the same molar amount.

該反応は室温下、冷却下あるいは加温下に行なうことが
できるが一般的には、通常O〜50℃、好ましくはO℃
〜室温であり、反応時間は通常3〜10時間である。
The reaction can be carried out at room temperature, cooling or heating, but is generally carried out at 0 to 50°C, preferably at 0°C.
to room temperature, and the reaction time is usually 3 to 10 hours.

上記各反応に於てはいずれも所望化合物を収率よく収得
できる。
In each of the above reactions, the desired compound can be obtained in good yield.

斯くして得られる本発明化合物を出発原料として用L・
例えば下式に示す反応を行なうことにより容易にシス−
6−ヘンアイコセンー11−オンを製造し得る。
Using the compound of the present invention thus obtained as a starting material, L.
For example, by performing the reaction shown in the following formula, cis-
6-heneicosen-11-one can be produced.

上記式中nは2又は3を示し、Xはハロゲン原子を示す
In the above formula, n represents 2 or 3, and X represents a halogen atom.

以下に本発明を更に明らかにするために実施例及び応用
例を掲げるが、本発明はこれに限定されるものではない
Examples and application examples are listed below to further clarify the present invention, but the present invention is not limited thereto.

実施例 3−デシル−2−シクロヘキセノン(式(IV)の化合
物)の製造 乾燥テトラヒドロフランにリチウム8707Qの少片を
加え、これに窒素気流下20〜30℃で攪拌しなから3
−エトキシ−2−シクロヘキセノン7fI及びn−デシ
ルブロマイド13.3Pの混合物を滴下する。
Example 3 - Preparation of decyl-2-cyclohexenone (compound of formula (IV)) A small piece of lithium 8707Q was added to dry tetrahydrofuran, and the mixture was stirred at 20-30°C under a stream of nitrogen.
A mixture of 7fI of -ethoxy-2-cyclohexenone and 13.3P of n-decyl bromide is added dropwise.

滴下後室温で1時間攪拌したのち過剰のリチウムをP去
し母液を冷希硫酸中に投じエーテル抽出を行なう。
After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and then excess lithium was removed by P, and the mother liquor was poured into cold dilute sulfuric acid for ether extraction.

エーテル溶液を飽和重曹水、次いで飽和食塩水で洗浄し
て硫酸マグネシウムで乾燥する。
The ether solution is washed with saturated aqueous sodium bicarbonate solution, then saturated brine, and dried over magnesium sulfate.

溶媒を留去し残渣を減圧蒸留して3デシル−2−シクロ
ヘキセノンを得る。
The solvent was distilled off and the residue was distilled under reduced pressure to obtain 3decyl-2-cyclohexenone.

収量9.9?;収率846%;沸点130〜132℃1
0.3mHg 3−デシル−2・3−エポキシシクロヘキサノン(式(
V)の化合物)の製造 3−デシル−2−シクロヘキセノン9.61’メタノー
ルH)mlに溶解し10°Cに冷却する。
Yield 9.9? ; Yield 846%; Boiling point 130-132℃1
0.3 mHg 3-decyl-2,3-epoxycyclohexanone (formula (
Preparation of compound V) 3-decyl-2-cyclohexenone was dissolved in 9.61 ml of methanol (H) and cooled to 10°C.

これに攪拌下30%の過酸化水素水16rulを滴下し
、次いで15〜20℃に維持しつつ6Nの水酸化ナトリ
ウム3.5mlを5分を要して加えたのち20〜25℃
で3時間攪拌する。
16 rules of 30% hydrogen peroxide solution was added dropwise to this while stirring, and then 3.5 ml of 6N sodium hydroxide was added over 5 minutes while maintaining the temperature at 15-20°C.
Stir for 3 hours.

反応液を水中に投じエーテルで抽出する。The reaction solution was poured into water and extracted with ether.

エーテル溶液を水、次いで飽和食塩水で洗浄した後硫酸
マグネシウムで乾燥する。
The ether solution is washed with water, then with saturated saline, and then dried over magnesium sulfate.

溶媒を留去し残渣を減圧蒸留して3−デシル2・3−エ
ポキシシクロヘキサノンを得る。
The solvent was distilled off and the residue was distilled under reduced pressure to obtain 3-decyl 2,3-epoxycyclohexanone.

収量9.1グ;収率90.4%;沸点125〜126℃
10.2mmHg l−ヘキサデシン−6−オン(式(M)の化合物)の製
造 塩化メチレン20m1及び酢酸10TILlに3−デシ
ル−2・3−エポキシシクロへキサノン5グを溶解し、
これに0〜2℃で攪拌下p−トルエンスルホニルヒドラ
ジド3,7りを一度に加え、次いで0〜2℃で3時間攪
拌し、更に室温で3時間攪拌する。
Yield: 9.1 g; Yield: 90.4%; Boiling point: 125-126°C
10.2 mmHg Production of l-hexadecyn-6-one (compound of formula (M)) Dissolve 5 g of 3-decyl-2,3-epoxycyclohexanone in 20 ml of methylene chloride and 10 TIL of acetic acid,
To this, 3.7 g of p-toluenesulfonyl hydrazide is added at once while stirring at 0 to 2°C, followed by stirring at 0 to 2°C for 3 hours, and further stirring at room temperature for 3 hours.

反応液を水中に投じn−へキサンで抽出を行なう。The reaction solution was poured into water and extracted with n-hexane.

n−ヘキサン溶液を水、飽和重曹水、飽和食塩水の順で
洗浄して硫酸マグネシウムで乾燥する。
The n-hexane solution is washed with water, saturated aqueous sodium bicarbonate, and saturated brine in this order, and dried over magnesium sulfate.

減圧濃縮して残渣を減圧蒸留して1−ヘキサデシン−6
−オンを得る。
Concentrate under reduced pressure and distill the residue under reduced pressure to obtain 1-hexadecine-6
- Get on.

収量411;収率87.2%;沸点122〜123℃/
0.8 mmHg 。
Yield 411; Yield 87.2%; Boiling point 122-123°C/
0.8 mmHg.

固化し、石油エーテルより再結晶して無色プリズム状晶
で得る。
It solidifies and is recrystallized from petroleum ether to give colorless prismatic crystals.

(融点27〜28℃)。Oエチルスルホニルヒドラジド
2.22を用いる以外は上記と同様にしてl−ヘキサデ
シン−6オン2.51を得る。
(Melting point 27-28°C). 2.51 of l-hexadecine-6one is obtained in the same manner as above except that 2.22 of O ethylsulfonyl hydrazide is used.

応用例 1−ヘキサデシン−6−オン−エチレンケタール(式〔
■〕の化合物)の製造 無水ベンゼン1001rLlに1−ヘキサデシン−6オ
ン3t1エチレンクリコール0.9?及ヒpトル工ンス
ルホン酸5m9を溶解し、水分離装置をつげて6時間還
流を行なう。
Application example 1-Hexadecin-6-one-ethylene ketal (formula [
■Production of compound) 1-hexadecin-6one 3t1 ethylene glycol 0.9? Then, 5 m9 of hypotonic sulfonic acid was dissolved, and a water separator was attached to the solution to reflux for 6 hours.

冷却後飽和重曹水、次いで飽和食塩水で洗浄して硫酸マ
グネシウムで乾燥する。
After cooling, it is washed with saturated sodium bicarbonate solution, then saturated brine, and dried over magnesium sulfate.

ベンゼンを留去し残渣を減圧蒸留して1−ヘキサデシン
−6−オン−エチレンケタールを得る。
Benzene is distilled off and the residue is distilled under reduced pressure to obtain 1-hexadecyn-6-one-ethylene ketal.

収量3.2グ;収率88.9%;沸点120〜125℃
10.3朋Hg 6−ヘンアイコジンー11−オン−エチレンケタール(
式〔■〕の化合物)の製造 乾燥テトラヒドロフラン15m1に1−ヘキサデシン−
6−オン−エチレンケタ−ル2.8rを溶解し、これに
氷冷却下に攪拌しつつn−ブチルリチウム(1,7モル
)のn−ヘキサン溶液6.6−を滴下する。
Yield: 3.2 g; Yield: 88.9%; Boiling point: 120-125°C
10.3 Hg 6-heneicodin-11-one-ethylene ketal (
Preparation of compound of formula [■]) Add 1-hexadecine to 15 ml of dry tetrahydrofuran.
2.8 liters of 6-one-ethylene ketal is dissolved, and 6.6 liters of a solution of n-butyllithium (1.7 mol) in n-hexane is added dropwise to this solution while stirring under ice cooling.

室温で15分間攪拌し、次いでこれにアミルブロマイド
3グの乾燥リン酸へキサメチルトリアミド溶液25TL
lを氷冷下撹拌しつつ滴下したのち水冷下に1時間攪拌
する。
Stir for 15 minutes at room temperature, then add 25 TL of a solution of 3 g of amyl bromide in dry phosphoric acid hexamethyltriamide.
1 was added dropwise while stirring under ice-cooling, and the mixture was stirred for 1 hour under water-cooling.

反応液を氷水中に投じn−ヘキサンで抽出を行なう。The reaction solution was poured into ice water and extracted with n-hexane.

n−ヘキサン溶液を水、飽和食塩水で洗浄して硫酸マグ
ネシウムで乾燥する。
The n-hexane solution is washed with water and saturated brine, and dried over magnesium sulfate.

溶媒を留去し残渣を減圧蒸留して6−ヘンアイコシン−
11−オン−エチレンケタールを得る。
The solvent was distilled off and the residue was distilled under reduced pressure to obtain 6-heneicosine.
11-one-ethylene ketal is obtained.

収量3.11収率88.6%;沸点165〜168℃1
0.3mmHg 6−ヘンアイコシン−11−オン(式〔■〕の化合物)
の製造 6−ヘンアイコジンー11−オン−エチレンケタール1
5グをテトラヒドロフラン15m1に溶解し、次いでこ
れに3Nの過塩素酸5mlを加えて冷蔵庫で一晩放置す
る。
Yield 3.11 Yield 88.6%; Boiling point 165-168℃1
0.3mmHg 6-heneicosin-11-one (compound of formula [■])
Production of 6-heneicodin-11-one-ethylene ketal 1
5 g was dissolved in 15 ml of tetrahydrofuran, then 5 ml of 3N perchloric acid was added thereto, and the mixture was left overnight in the refrigerator.

テトラヒドロフランを留去し残渣を水で希釈してエーテ
ル抽出を行なう。
Tetrahydrofuran is distilled off, the residue is diluted with water, and extracted with ether.

エーテル溶液を飽和重曹水、次いで飽和食塩水で洗浄し
て硫酸マグネシウムで乾燥する。
The ether solution is washed with saturated aqueous sodium bicarbonate solution, then saturated brine, and dried over magnesium sulfate.

エーテルを留去し残漬を減圧蒸留して6−ヘンアイコシ
ン11−オンを得る。
The ether is distilled off and the residue is distilled under reduced pressure to obtain 6-heneicosine 11-one.

収量1.2グ;収率91,6%;沸点145〜150℃
/ 0.2 mm Hgシス−6−ヘンアオコセン−1
1−オン(式〔X〕の化合物)の製造 6−ヘンアイコシン−11−オン0.9rをメタノール
15m1に溶解し、次いでこれに5%パラジウム−硫酸
バリウム150■及びキノリン2滴を加え振とう下室温
常圧で水素を吸収させる。
Yield 1.2 g; Yield 91.6%; Boiling point 145-150°C
/ 0.2 mm Hgcis-6-henaocosene-1
Preparation of 1-one (compound of formula [X]) Dissolve 0.9r of 6-heneicosin-11-one in 15ml of methanol, then add 150ml of 5% palladium-barium sulfate and 2 drops of quinoline and shake. Absorb hydrogen at room temperature and normal pressure.

触媒を1去し母液を減圧濃縮する。The catalyst was removed and the mother liquor was concentrated under reduced pressure.

残渣をエーテルに溶解し、希塩酸、飽和重曹水、飽和食
塩水の順で洗浄して硫酸マグネシウムで乾燥する。
The residue is dissolved in ether, washed successively with dilute hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine, and dried over magnesium sulfate.

エーテルを留去し残渣を減圧蒸留してシス−6−ヘンア
オコセン−11−オンを得る。
The ether was distilled off and the residue was distilled under reduced pressure to obtain cis-6-henaocosen-11-one.

Claims (1)

【特許請求の範囲】 1式 で表わされる1−ヘキサデシン−6−オン。[Claims] 1 set 1-Hexadecin-6-one represented by:
JP6915976A 1976-06-11 1976-06-11 1-hexadecin-6-one Expired JPS5831330B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP6915976A JPS5831330B2 (en) 1976-06-11 1976-06-11 1-hexadecin-6-one

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP6915976A JPS5831330B2 (en) 1976-06-11 1976-06-11 1-hexadecin-6-one

Publications (2)

Publication Number Publication Date
JPS52153906A JPS52153906A (en) 1977-12-21
JPS5831330B2 true JPS5831330B2 (en) 1983-07-05

Family

ID=13394623

Family Applications (1)

Application Number Title Priority Date Filing Date
JP6915976A Expired JPS5831330B2 (en) 1976-06-11 1976-06-11 1-hexadecin-6-one

Country Status (1)

Country Link
JP (1) JPS5831330B2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1047378C (en) * 1996-07-01 1999-12-15 北京工业大学 Method for synthesizing sex information hormone of bollworm

Also Published As

Publication number Publication date
JPS52153906A (en) 1977-12-21

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