9(11)-didehydroestradiol-17β 3-methyl ether | 6702-61-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 9(11)-didehydroestradiol-17β 3-methyl ether
• 英文别名: 3-methoxy-13β-methylgona-1,3,5(10),9(11)-tetraen-17β-ol；3-Methoxy-17β-hydroxy-oestra-1,3,5(10),9(11)-tetraen；3-Methoxy-Oestra-1,3,5(10),9(11)-tetraen-17β-ol；3-Methoxyestra-1,3,5(10),9(11)-tetraen-17β-ol；(8S,13S,14S,17S)-3-methoxy-13-methyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-17-ol
• CAS: 6702-61-0
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: HAEKHUDOKPDLPV-XWSJACJDSA-N

物化性质

• 熔点：
  71-73 °C
• 沸点：
  448.2±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9(11)-didehydroestradiol-17β 3-methyl ether 生成 estradiol methyl ether
  参考文献：
  名称：

  BARNIKOL-OETTLER, K.;TEICHMUELLER, G.

  摘要：

  DOI：
• 作为产物：
  描述：

  3-methoxy-estra-1,3,5(10),8(9),14(15)-pentaene-17-one 在 palladium/alumina 盐酸 、 sodium tetrahydroborate 、 氢气 作用下， 以 吡啶 、 甲醇 、 乙醇 、 丙酮 为溶剂， 生成 9(11)-didehydroestradiol-17β 3-methyl ether
  参考文献：
  名称：

  Hainaut,D.; Bucourt,R., Bulletin de la Societe Chimique de France, 1978, vol. , p. 119 - 125

  摘要：

  DOI：

文献信息

• Process of making gona-1,3,5(10),9(11)-tetraenes
  申请人：VEB Jenapharm

  公开号：US04029648A1

  公开（公告）日：1977-06-14

  Gona-1,3,5(10),9(11)-tetraenes having the formula ##STR1## IN WHICH FORMULA N IS 1 OR 2, R.sup.1 is a hydrogen, hydroxy, alkoxy, or alkanoyl substituent, R.sup.2 is a hydrogen, alkoxy, acetoxy, alkyl, akenyl, or alkynyl substituent, or a substituent having the formula --CH.sub.2 X in which X is a halogen, pseudohalogen, or O-alkyl substituent, or R.sup.1 or R.sup.2 together are oxygen, or a methyleneoxy or ethylenedioxy substituent, R.sup.3 is a hydroxy, alkoxy, alkanoyl, or alkoxymethyleneoxy substituent, and R.sup.4 is a methyl or ethyl substituent, Are made from gona-1,3,5(10)trienes by electrolysis of a solution thereof in water and/or a primary or secondary alcohol in the presence of an electroconductive compound. The gona-1,3,5(10),9(11)-tetraenes are intermediates for the production of steroidal pharmaceuticals for fertility control in human and animal therapeutics.

  Gona-1,3,5(10),9(11)-四烯类化合物，其具有公式##STR1##，其中N为1或2，R1为氢、羟基、烷氧基或烷酰基取代基，R2为氢、烷氧基、乙酰氧基、烷基、烯基或炔基取代基，或者具有公式--CH2X的取代基，其中X为卤素、拟卤素或O-烷基取代基，或者R1和R2共同为氧，或者为亚甲基氧基或乙二氧基取代基，R3为羟基、烷氧基、烷酰基或烷氧基亚甲基氧基取代基，R4为甲基或乙基取代基，可以通过gon a-1,3,5(10)三烯的水和/或一级或二级醇溶液的电解制得，在存在电导化合物的情况下。Gona-1,3,5(10),9(11)-四烯类化合物用于生产用于人类和动物治疗中生育控制的甾体药物。
• Chromogenic reactions of steroids with strong acids. IX. Behavior of estrone methyl ether in concentrated sulfuric acid.
  作者：TOSHIAKI MIURA、MICHIYA KIMURA

  DOI：10.1248/cpb.26.171

  日期：——

  The behavior of estrone methyl ether (V) in strong acid was studied, in order to elucidate the mechanism of the Kober color reaction. When V was dissolved into concentrated sulfuric acid, a maximum absorption gradually appeared at 465 nm which was then transferred to 452 nm with elapse of time. On the other hand, 3-methoxy-17α-methylestra-1, 3, 5 (10), 9 (11)-tetraen-17β-ol (XIIIb) immediately gave the chromophoric cation χ-465 (VIIb) in concentrated sulfuric acid. Similarly, 3-methoxyestra-1, 3, 5 (10), 9 (11)-tetraen-17β-ol (XIIIa) gave the cation χ-364 (XIVa) which changed in turn to χ-465 (VIIa). Sulfonation gradually occurred at C (2)s of VIIa and VIIb in the same acid to give the corresponding cations XIXa and XIXb ; the maximum absorption at 465 nm altered to 452 nm. The mechanism of the conversion of V into the C (2)-sulfonated χ-465 (XIXa) was elucidated from these behavior of XIIIa and XIIIb in concentrated sulfuric acid.

  研究了雌酮甲醚(V)在强酸中的行为，以阐明Kober显色反应的机理。当V溶解到浓硫酸中时，在465 nm处逐渐出现最大吸收，然后随着时间的推移转移到452 nm。另一方面，3-methoxy-17α-methylestra-1, 3, 5 (10), 9 (11)-tetraen-17β-ol (XIIIb) 在浓硫酸中立即产生发色阳离子 χ-465 (VIIb) 。类似地，3-methoxyestra-1, 3, 5 (10), 9 (11)-tetraen-17β-ol (XIIIa) 得到阳离子 χ-364 (XIVa)，其又变为 χ-465 (VIIa)。在相同的酸中，VIIa和VIIb的C(2)处逐渐发生磺化，得到相应的阳离子XIXa和XIXb； 465 nm 处的最大吸收变为 452 nm。从XIIIa和XIIIb在浓硫酸中的这些行为阐明了V转化成C(2)-磺化χ-465(XIXa)的机制。
• A [4+1] cyclopentannulation route to ring a aromatic, C(1)-C(11) methano-bridged steroids
  作者：H. Künzer、G. Sauer、R. Wiechert

  DOI：10.1016/s0040-4039(00)79764-4

  日期：1991.7

  In a novel, one-pot [4+1] cyclopentannulation procedure, the steroidal olefin 2 and CH20 are converted into the corresponding C(1)-C(11) methano-bridged derivative 3 by two sequential Lewis acid-promoted electrophilic substitutions. Birch reduction of the olefin 3, followed by removal of the protecting groups, affords 1,11α-methano-9β-estra-l,3,5(10)-triene- 3,17β-diol (6).

  在一种新颖的，一锅式[4 + 1]环戊烯醛化工艺中，甾体烯烃2和CH 2 0通过两个连续的路易斯酸促进的亲电基团转化为相应的C（1）-C（11）甲醇桥连衍生物3换人。烯烃3的桦木还原，然后除去保护基，得到1,11α-甲基-9β-雌-1,3,5（10）-三烯-3,17β-二醇（6）。
• Direct conversion of 13β-alkylgonatetraenes into 13β-alkylgon-4-en-3-ones
  作者：Panicker Bijoy、Uma Ramachandran、G. S. R. Subba Rao

  DOI：10.1039/p19940002331

  日期：——

  Birch reduction of 8,9-didehydroestradiol-17 beta 3-methyl ether 1 or 9(11)-didehydroestradiol-17 beta 3-methyl ether 2 followed by acid hydrolysis results in a mixture of 19-nortestosterone 8 and 19-nor-9 beta, 10 alpha-testosterone 9 in varying amounts. However, reduction of their acetates with sodium or lithium, tert-butyl alcohol in liquid ammonia and in the presence of aniline affords exclusively 19-nortestosterone. Similarly, 18a-homo-19-nortestosterone 12 is prepared from the acetate of 18a-homoestradiol-17 beta 3-methyl ether, 10.
• US4029648A
  申请人：——

  公开号：US4029648A

  公开（公告）日：1977-06-14