(4R)-4-[(2R)-2-(hydroxymethyl)butyl]oxolan-2-one | 378243-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R)-4-[(2R)-2-(hydroxymethyl)butyl]oxolan-2-one
• CAS: 378243-88-0
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: GMXSQQJGKNIYSN-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-4-[(2R)-2-(hydroxymethyl)butyl]oxolan-2-one 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal copper(l) iodide 、 正丁基锂 、 sodium azide 、 氨 、 氢气 、 叔丁基锂 、 sodium ethanolate 、 二甲基氯化铝 、 sodium hydride 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (4R,6R)-2-[3-(cyanomethyl)-1H-indol-2-yl]-6-ethyl-4-(phenylmethoxymethyl)azepane-1-carboxylate
  参考文献：
  名称：

  A stereoselective synthesis of naturally occurring (+)-20 R -dihydrocleavamine by photo-[2+2]-cycloreversion

  摘要：

  A stereoselective synthesis of (+)-20R-dihydrocleavamine, an alkaloid from Pandaca eusepala and Tabernamontana eglandulose, has been developed using an enantiopure tricyclic ketone accessible from a meso precursor by employing a photo-[2+2]-cycloreversion reaction as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01538-6
• 作为产物：
  描述：

  (1R,2S,5S,6S,7S,8R)-7,8-dihydroxytricyclo[4.2.1.02,5]nonan-3-one 在 platinum(IV) oxide sodium periodate 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (4R)-4-[(2R)-2-(hydroxymethyl)butyl]oxolan-2-one
  参考文献：
  名称：

  A stereoselective synthesis of naturally occurring (+)-20 R -dihydrocleavamine by photo-[2+2]-cycloreversion

  摘要：

  A stereoselective synthesis of (+)-20R-dihydrocleavamine, an alkaloid from Pandaca eusepala and Tabernamontana eglandulose, has been developed using an enantiopure tricyclic ketone accessible from a meso precursor by employing a photo-[2+2]-cycloreversion reaction as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01538-6

文献信息

• Flexible Access to Monoterpenoid Indole Alkaloids Using a Cyclopentanoid Chiral Building Block
  作者：Yoshiharu Iwabuchi、Masato Hayashi、Atsushi Satoh、Masatoshi Shibuya、Kunio Ogasawara

  DOI：10.3987/com-08-s(f)120

  日期：——

  Expedient, diasterocontrolled transformations of 1 to the key synthetic intermediate of corynanthe, iboga, and aspidosperma-class of monoterpenoid indole alkaloids which led up to a formal synthesis of (+)-20R-dihydrocleavamine, (-)-eburnamonine, and a total synthesis of (+)-aspidospermidine (2) have been demonstrated.
• A stereoselective synthesis of naturally occurring (+)-20 R -dihydrocleavamine by photo-[2+2]-cycloreversion
  作者：Regina Mikie Kanada、Kunio Ogasawara

  DOI：10.1016/s0040-4039(01)01538-6

  日期：2001.10

  A stereoselective synthesis of (+)-20R-dihydrocleavamine, an alkaloid from Pandaca eusepala and Tabernamontana eglandulose, has been developed using an enantiopure tricyclic ketone accessible from a meso precursor by employing a photo-[2+2]-cycloreversion reaction as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.