Δ⁴-Cholesten-3-one ethylene dithioacetal | 2791-51-7

• 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: Δ⁴-Cholesten-3-one ethylene dithioacetal
• 英文别名: Cholest-4-en-3-one ethylene dithioacetal；cholest-4-en-3-one dithioketal；(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]spiro[1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dithiolane]
• CAS: 2791-51-7
• 化学式: C₂₉H₄₈S₂
• 分子量: 460.832
• InChiKey: ZVQGNXVEMQLIQF-OKPKYCIKSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  548.6±45.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Δ⁴-Cholesten-3-one ethylene dithioacetal 在 水 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙醇 为溶剂， 反应 0.17h， 生成 4-胆甾烯-3-酮
  参考文献：
  名称：

  Rabinowitz, Michael H.; Djerassi, Carl, Journal of the American Chemical Society, 1992, vol. 114, # 1, p. 304 - 317

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-butyl(((6R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-methylheptyl)oxy)diphenylsilane 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 pyridinium chlorochromate 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氯仿 、 二甲基亚砜 为溶剂， 反应 127.42h， 生成 Δ⁴-Cholesten-3-one ethylene dithioacetal
  参考文献：
  名称：

  Rabinowitz, Michael H.; Djerassi, Carl, Journal of the American Chemical Society, 1992, vol. 114, # 1, p. 304 - 317

  摘要：

  DOI：

文献信息

• Highly Efficient Dithioacetalization of Carbonyl Compounds Catalyzed with Iodine Supported on Neutral Alumina
  作者：Nabajyoti Deka、Jadab C. Sarma

  DOI：10.1246/cl.2001.794

  日期：2001.8

  Aldehydes and ketones are protected as their corresponding dithioacetals with ethane-1,2-dithiol in the presence of a catalytic amount of iodine supported on neutral alumina surface. This is a high yielding method of carbonyl group protection under mild, neutral and solvent free conditions.

  醛和酮在中性铝土表面上以乙炔-1,2-二硫醇的对应二硫缩醛形式得到保护，反应中使用了少量的碘作为催化剂。这是一种在温和、中性和无溶剂条件下高产率的羰基保护方法。
• Synthesis of Steroidal 3,5-Dieno[3,4-<i>b</i>](5,6-dihydro-1,4-dithiins)
  作者：John R. Williams、Phuoc B. Tran

  DOI：10.1055/s-1988-27678

  日期：——

  Reaction of steroidal 4-en-3-one ethylene dithioacetals with phenylselenenyl chloride in dichloromethane yields steroidal 3,5-dieno[3,4-b] (5,6-dihydro-1,4-dithiins).

  类固醇 4-en-3-one 亚乙基二硫缩醛与苯基硒基氯在二氯甲烷中反应，生成类固醇 3,5-二烯[3,4-b]（5,6-二氢-1,4-二硫英）。
• Steroids and Walden inversion. Part LXIII. Substitution reactions of the 5α-cholestan-4-ols: a further example of Walden retention
  作者：C. W. Shoppee、R. E. Lack、S. C. Sharma

  DOI：10.1039/j39680002083

  日期：——

  5α-Cholestan-4α-ol reacts with phosphorus pentachloride or thionyl chloride to give 4α-chloro-5α-cholestane with much elimination product, and with phosphorus pentabromide at 0° it gives 4α-bromo-5α-cholestane, in each case with retention of configuration. 5α-Cholestan-4β-ol, with phosphorus pentachloride or phosphorus pentabromide in chloroform at 20°, or with thionyl chloride, yields mainly cholest-4-ene;

  5α-胆甾醇4α-醇与五氯化磷或亚硫酰氯反应生成具有大量消除产物的4α-氯5α-胆甾烷，与五溴化磷在0°时生成4α-溴5α-胆甾烷，在每种情况下均具有保留配置。5α-Cholestan-4β-ol，与在氯仿中的五氯化磷或五溴化磷在20°C或亚硫酰氯形成，主要生成胆甾4-烯。在80°C的苯中使用五氯化磷生成4β，5α-二氯胆甾烷。
• Reduction of a δ⁴-Steroid with Diborane
  作者：Cecilia D'Alessandro、Sergio Giacopello、Alicia M. Seldes、Mónica E. Deluca

  DOI：10.1080/00397919508011818

  日期：1995.9

  Abstract Reported here is a boron process equivalent to stereoselective olefin reduction and concomitant protecting group cleavage.

  摘要这里报道了一种硼工艺，相当于立体选择性烯烃还原和伴随的保护基裂解。
• Differentiation between carbonyls and acetals in 1,3-dithiane and 1,3-dithiolane synthesis catalyzed by organotin triflates
  作者：Tsuneo Sato、Junzo Otera、Hitosi Nozaki

  DOI：10.1021/jo00070a038

  日期：1993.8

  Carbonyls and acetals are converted to 1,3-dithianes and -dithiolanes upon treatment with 2-stanna-1,3-dithianes and -dithiolanes under catalysis by organotin triflates. In these competition reactions, various types of carbonyls and acetals are differentiated. Aldehydes react preferentially over ketones, but the preference is completely reversed in the competition reactions between the corresponding acetals and ketals. The reactivity of aliphatic aldehydes is greater than that of the acetals of aliphatic aldehydes and ketones. Conversely, an aromatic acetal is more reactive than its parent aldehyde. In the competition between aromatic and aliphatic aldehydes, the reaction of the latter predominates. However, aromatic acetals react preferentially over aliphatic acetals. Ketones of different types are also differentiated. No such discrimination can be achieved by conventional methods. Organotin triflates are capable of detecting subtle differences in the reactivity of carbonyls and acetals. Such unique differentiation can be explained in terms of the dependence of the reaction path on the substrate: the reactions of carbonyls are initiated by coordination to tin, whereas the reactions of acetals proceed via oxocarbenium ion intermediates.