Cholesteryl-α-chloropropionate

• 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: Cholesteryl-α-chloropropionate
• 英文别名: cholesteryl 2-chloropropionate；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 2-chloropropanoate
• 化学式: C₃₀H₄₉ClO₂
• 分子量: 477.171
• InChiKey: XOLVVFSHDULKRS-VAEUHUSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二苯基氯化膦 、 硼烷四氢呋喃络合物 、 Cholesteryl-α-chloropropionate 在 五甲基二乙烯三胺 作用下， 以 乙腈 为溶剂， 以44 %的产率得到(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-(diphenylphosphaneyl)propanoate borane
  参考文献：
  名称：

  氯膦与有机卤化物的交叉电 C−PIII 偶联：通过磷键合实现光诱导 PIII 和氨基烷基自由基生成

  摘要：

  在可见光照射下，中性磷元素键合 (PnB) 能够实现从烷基胺到氯膦的单电子转移 (SET)。该过程产生 P III自由基和氨烷基自由基。随后，氨基烷基通过卤素原子转移（XAT）激活CX键。结果，实现了氯膦和有机卤化物之间的交叉亲电子CP III偶联。

  DOI：

  10.1002/anie.202310764
• 作为产物：
  描述：

  2-氯丙酰氯 、 胆固醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到Cholesteryl-α-chloropropionate
  参考文献：
  名称：

  3-Alkyl-6-Chloro-2-pyrones:  Selective Inhibitors of Pancreatic Cholesterol Esterase

  摘要：

  A series of 3-alkyl-6-chloro-2-pyrones with cyclohexane rings tethered to the S-position was synthesized. The tether ranged from 0 to 4 methylene units. Inhibition of pancreatic-cholesterol esterase by this series of pyrones was markedly dependent upon the length of the tether. Dissociation constants as low as 25 nM were observed for 6-chloro-3-(1-ethyl-2-cyclohexyl)-2-pyranone. This class of cholesterol esterase inhibitors functioned as simple competitive inhibitors of substrate binding rather than as suicide substrates or active site inactivators. Trypsin and chymotrypsin were not strongly inhibited by this class of pyrones. Selectivities for cholesterol esterase were greater than 10(3). This is in contrast to 3-aryl-6-chloro-2-pyrones which are nonselective, irreversible inactivators of serine hydrolases, Thus, replacement of the 3-aryl group by an appropriately tethered 3-alkyl ring can produce highly selective inhibitors of cholesterol esterase. A second series of halogen-containing esters was prepared in which cholesterol was esterified with alpha-haloacyl halides. These haloesters were simple substrates of cholesterol esterase with no evidence of irreversible inactivation.

  DOI：

  10.1021/jm990309x

文献信息

• Yano; Nabata; Aoki, Molecular Crystals and Liquid Crystals (1969-1991), 1980, vol. 70, # 1-4, p. 163 - 168
  作者：Yano、Nabata、Aoki

  DOI：——

  日期：——