5α-cholestan-3α-yl chloroethanoate | 164120-52-9

• 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: 5α-cholestan-3α-yl chloroethanoate
• 英文别名: [(3R,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] 2-chloroacetate
• CAS: 164120-52-9
• 化学式: C₂₉H₄₉ClO₂
• 分子量: 465.16
• InChiKey: WUBOZGDSEKAKCR-MSKYUDLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 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：

  5α-cholestan-3α-yl chloroethanoate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以47%的产率得到5α-cholestan-3α-yl azidoethanoate
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of water-soluble, dendritic derivatives of epimeric 5α-cholestan-3-amines and 5α-cholestan-3-yl aminoethanoates

  摘要：

  To examine the effect of negatively charged steroidal amphiphiles on antimicrobial activity, two pairs of epimeric, dendritic tricarboxylato amphiphiles -4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yl)ureido]heptanedioic acid (1) and 4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yloxycarbonylmethyl)ureido]heptanedioic acid (2) - were synthesized. Abroad antimicrobial screen of 11 microbes revealed that these amphiphiles only showed good activity against a methicillin -resistant isolate of Staphylococcus aureus (MRSA) and modest activity against an unrelated strain of S aureus The best activity a minimal inhibitory concentration (MIC) of 27 mu M, was found for the 3 beta epimer of 1 against MRSA. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.04.001
• 作为产物：
  描述：

  3β-胆甾烷醇 在 sodium benzoate 、 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 三氟乙酸 、 苯 为溶剂， 反应 32.0h， 生成 5α-cholestan-3α-yl chloroethanoate
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of water-soluble, dendritic derivatives of epimeric 5α-cholestan-3-amines and 5α-cholestan-3-yl aminoethanoates

  摘要：

  To examine the effect of negatively charged steroidal amphiphiles on antimicrobial activity, two pairs of epimeric, dendritic tricarboxylato amphiphiles -4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yl)ureido]heptanedioic acid (1) and 4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yloxycarbonylmethyl)ureido]heptanedioic acid (2) - were synthesized. Abroad antimicrobial screen of 11 microbes revealed that these amphiphiles only showed good activity against a methicillin -resistant isolate of Staphylococcus aureus (MRSA) and modest activity against an unrelated strain of S aureus The best activity a minimal inhibitory concentration (MIC) of 27 mu M, was found for the 3 beta epimer of 1 against MRSA. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.04.001

文献信息

• Mitsunobu acylation of sterically congested secondary alcohols by N,N,N′,N′-tetramethylazodicarboxamide-tributylphosphine reagents
  作者：Tetsuto Tsunoda、Yoshiko Yamamiya、Yumi Kawamura、Shô Itô

  DOI：10.1016/0040-4039(95)00299-r

  日期：1995.4

  Four secondary alcohols of different steric environment reacted with five carboxylic acids of different acidity in the presence of N,N,N',N'-tetramethylazodicarboxamide and tributylphosphine to give the corresponding epi-esters in better yield than with diethyl azodicarboxylate-triphenylphosphine in most cases. Of special merit is the combination of the new reagent system with p-methoxybenzoic acid to achieve complete inversion of sterically congested secondary alcohols.