pergularin

• 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: pergularin
• 英文别名: 1-[(3S,8R,9S,10R,12R,13S,14S,17S)-3,12,14,17-tetrahydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• 化学式: C₂₁H₃₂O₅
• 分子量: 364.482
• InChiKey: VJMNSJUASLIQEP-UPFSRWTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  pergularin 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以66.667%的产率得到
  参考文献：
  名称：

  Scalable C–H Oxidation with Copper: Synthesis of Polyoxypregnanes

  摘要：

  Steroids bearing C12 oxidations are widespread in nature, yet only one preparative chemical method addresses this challenge in a low-yielding and not fully understood fashion: Schonecker's Cu-mediated oxidation. This work shines new light onto this powerful C-H oxidation method through mechanistic investigation, optimization, and wider application. Culminating in a scalable, rapid, high-yielding, and operationally simple protocol, this procedure is applied to the first synthesis of several parent polyoxypregnane natural products, representing a gateway to over 100 family members.

  DOI：

  10.1021/jacs.5b09463
• 作为产物：
  描述：

  3α,5-cycloandrost-6-en-17-one 在 bis(acetylacetonato)manganese(II) 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 氢溴酸 、 叔丁基锂 、 氧气 、 palladium diacetate 、 silica gel 、 对甲苯磺酸 、 溶剂黄146 、 sodium ascorbate 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 、 正戊烷 为溶剂， 反应 96.66h， 生成 pergularin
  参考文献：
  名称：

  Scalable C–H Oxidation with Copper: Synthesis of Polyoxypregnanes

  摘要：

  Steroids bearing C12 oxidations are widespread in nature, yet only one preparative chemical method addresses this challenge in a low-yielding and not fully understood fashion: Schonecker's Cu-mediated oxidation. This work shines new light onto this powerful C-H oxidation method through mechanistic investigation, optimization, and wider application. Culminating in a scalable, rapid, high-yielding, and operationally simple protocol, this procedure is applied to the first synthesis of several parent polyoxypregnane natural products, representing a gateway to over 100 family members.

  DOI：

  10.1021/jacs.5b09463

文献信息

• Scalable C–H Oxidation with Copper: Synthesis of Polyoxypregnanes
  作者：Yi Yang See、Aaron T. Herrmann、Yoshinori Aihara、Phil S. Baran

  DOI：10.1021/jacs.5b09463

  日期：2015.11.4

  Steroids bearing C12 oxidations are widespread in nature, yet only one preparative chemical method addresses this challenge in a low-yielding and not fully understood fashion: Schonecker's Cu-mediated oxidation. This work shines new light onto this powerful C-H oxidation method through mechanistic investigation, optimization, and wider application. Culminating in a scalable, rapid, high-yielding, and operationally simple protocol, this procedure is applied to the first synthesis of several parent polyoxypregnane natural products, representing a gateway to over 100 family members.