地诺孕素EP杂质H | 16669-06-0

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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
• 中文名称: 地诺孕素EP杂质H
• 英文名称: 2-((8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)acetonitrile
• 英文别名: 17α-cyanomethyl-1,3,5(10)-estratriene-3,17-diol；17α-cyanomethylestra-1,3,5(10)-triene-3,17-diol；STS 433；J 540；17α-Cyan-methyl-3,17β-oestradiol；17|A-Cyanomethylestra-1,3,5(10)-triene-3,17|A-diol；2-[(8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]acetonitrile
• CAS: 16669-06-0
• 化学式: C₂₀H₂₅NO₂
• 分子量: 311.424
• InChiKey: UJIUKBNBJLRRKB-SWBPCFCJSA-N

物化性质

• 沸点：
  528.3±50.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  炔雌醇 在 三(2-呋喃基)膦 、 [Rh(hydridotris(pyrazolyl)borate)(C2H4)2] 、 叔丁基肼 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以75%的产率得到地诺孕素EP杂质H
  参考文献：
  名称：

  TpRh（C 2 H 4）2 / P（2-呋喃基）3催化将3,3,3-三取代丙-1-炔与叔丁基肼转化为3,3,3-三取代丙腈

  摘要：

  TpRh（C 2 H 4）2（Tp =三（吡唑-1-基）硼酸酯）和P（2-呋喃基）3的组合催化叔烷基取代的炔烃与叔丁基肼的反应，导致形成3，3，3-三取代的丙腈衍生物。该反应体系适用于1，1-二取代的炔丙醇和胺，分别得到相应的β-氰醇和β-氨基腈。催化循环涉及形成乙烯基亚乙基络合物作为关键中间体。

  DOI：

  10.1021/acs.joc.6b00116

文献信息

• Species differences in biotransformation of 17α-cyanomethylestradiol 3-methyl ether
  作者：G. Hobe、R. Schön、W. Schade

  DOI：10.1016/0039-128x(80)90013-6

  日期：1980.8

  Following oral administration of 9,11-3H-17 alpha-cyanomethylestra-1,3,5(10)-triene-3,17-diol 3-methyl ether, urinary metabolites were studied in man, baboon, beagle dog, minipig and rat. The metabolite pattern revealed remarkable species differences, especially in quantitative respects. 17 alpha-Cyanomethylestra-1,3,5(10)triene-3,17-diol, 17 alpha-cyanomethylestra-1,3,5(10)-triene-2,3,17-triol 2-methyl ether, 17 alpha-hydroxymethylestra-1,3,5(10)-triene-3,17-diol and 17 alpha-cyanomethylestra-1,3,5(10)-triene-3,16 xi, 17-triol were isolated as principal metabolites. In rat bile, a metabolite was tentatively identified as a gamma-lactone of a 17 alpha-carboxymethyl-16 alpha-hydroxy compound.
• Horhold; Hubner; Ponsold, Pharmazie, 1975, vol. 30, # 1, p. 35 - 41
  作者：Horhold、Hubner、Ponsold、et al.

  DOI：——

  日期：——
• Microbial transformation of 17α-cyanomethyl-17-hydroxy-4,9-estradien-3-one (STS 557) and 17α-cyanomethyl-19-nortestosterone by Mycobacterium smegmatis
  作者：G. Hobe、R. Schön、C. Hörhold、M. Hübner、W. Schade、K. Schubert

  DOI：10.1016/0039-128x(82)90064-2

  日期：1982.4

  Microbial transformation of the new progestagen STS 557 (17 alpha-cyanomethyl-17-hydroxy-4,9-estradien-3-one) by Mycobacterium smegmatis yielded predominantly ring A-aromatized compounds: 17 alpha-cyanomethyl-1,3,5(10),9(11)-estratetraene-3, 17-diol, 17 alpha-cyanomethyl-1,3,5(10)-estratriene-3,17-diol and the corresponding 3-methyl ethers. The analogous compound without the 9(10) double bond, 17 alpha-cyanomethyl-19-nortestosterone, was transformed mainly to 5 alpha-hydrogenated metabolites: 17 alpha-cyanomethyl-17-hydroxy-5 alpha-estran-3-one, 17 alpha-cyanomethyl-17-hydroxy-5 alpha-1-estren-3-one, 17 alpha-cyanomethyl-5 alpha-estrane-3 alpha, 17-diol, and 17 alpha-cyanomethyl-5 alpha-estrane-3 beta, 17-diol. From these results, it is concluded that 4,9-dien-3-oxo compounds are not substrates for enzymatic 5 alpha-hydrogenation.
• Nitrile hydratase from Rhodococcus erythropolis: Metabolization of steroidal compounds with a nitrile group
  作者：Günter Kaufmann、Horst Dautzenberg、Harry Henkel、Gerd Müller、Thomas Schäfer、Bernd Undeutsch、Michael Oettel

  DOI：10.1016/s0039-128x(99)00028-8

  日期：1999.8

  The progestin dienogest (17 alpha-cyanomethyl-17 beta-hydroxy-estra-4,9-dien-3-one) was metabolized by the nitrile hydratase-containing microorganism Rhodococcus erythropolis. An enzymatic hydrolysis of the nitrile group at the 17 alpha-side chain was intended to obtain novel derivatives and to test them for progesterone receptor affinity. In contrast to the rapid enzymatic hydrolysis of nonsteroidal nitriles, the nitrile group of dienogest was cleaved very slowly. The dominant reaction was an aromatization of ring A. After prolonged fermentation, the 17 alpha-acetamido derivatives of estradiol and of 9(11)-dehydroestradiol were formed. Three of the metabolites were also prepared synthetically. They were tested for hormonal activity by assessing their binding to progesterone and estrogen receptors in vitro. Neither the aromatized 17 alpha-acetamido derivatives nor the dienogest derivative 17 alpha-acetamido-17 beta-hydroxy-estra-4,9-dien-3-one, which was prepared synthetically only, exhibited affinity for the progesterone receptor. (C) 1999 Elsevier Science Inc. All fights reserved.