di-t-butyl (R)-2-(2-benzyl-3-hydroxypropyl)malonate | 1353991-03-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: di-t-butyl (R)-2-(2-benzyl-3-hydroxypropyl)malonate
• 英文别名: (R)-di-t-butyl 2-(2-benzyl-3-hydroxypropyl)malonate；ditert-butyl 2-[(2R)-2-benzyl-3-hydroxypropyl]propanedioate
• CAS: 1353991-03-3
• 化学式: C₂₁H₃₂O₅
• 分子量: 364.482
• InChiKey: AJOOWEMHNRNEDU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  di-t-butyl (R)-2-(2-benzyl-3-hydroxypropyl)malonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟甲烷磺酰氯 作用下， 以 氯仿 为溶剂， 反应 3.5h， 以70%的产率得到di-t-butyl (S)-4-benzyldihydrofuran-2,2(3H)-dicarboxylate
  参考文献：
  名称：

  Powerful Amino Diol Catalyst for Effecting the Direct Asymmetric Conjugate Addition of Aldehydes to Acrylates

  摘要：

  Di-tert-butyl methylenemalonate (1) could be employed as a reactive equivalent of a three-carbon Michael acceptor such as acrylate in a direct asymmetric conjugate addition of aldehydes catalyzed by an axially chiral amino diol (S)-3a. Furthermore, acrylate, an unexplored and challenging substrate in enamine catalysis, has also been successfully employed in asymmetric conjugate addition reaction. Relatively inert acrylate is doubly activated by polyfluoroalkyl group of 2 and the hydroxyl group on the axially chiral amino diol catalyst (S)-3b, giving corresponding conjugate adducts in high yield with excellent enantiomeric excess. The obtained conjugate addition products were readily converted to synthetically useful and important chiral building blocks.

  DOI：

  10.1021/ja307668b
• 作为产物：
  描述：

  di-tert-butyl methylenemalonate 在 sodium tetrahydroborate 、 [8-(hydroxydiphenylmethyl)-1,11-dimethoxy-6,7-dihydro-5H-dibenzo[c,e]azepin-4-yl]diphenylmethanol 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.5h， 生成 di-t-butyl (R)-2-(2-benzyl-3-hydroxypropyl)malonate
  参考文献：
  名称：

  Powerful Amino Diol Catalyst for Effecting the Direct Asymmetric Conjugate Addition of Aldehydes to Acrylates

  摘要：

  Di-tert-butyl methylenemalonate (1) could be employed as a reactive equivalent of a three-carbon Michael acceptor such as acrylate in a direct asymmetric conjugate addition of aldehydes catalyzed by an axially chiral amino diol (S)-3a. Furthermore, acrylate, an unexplored and challenging substrate in enamine catalysis, has also been successfully employed in asymmetric conjugate addition reaction. Relatively inert acrylate is doubly activated by polyfluoroalkyl group of 2 and the hydroxyl group on the axially chiral amino diol catalyst (S)-3b, giving corresponding conjugate adducts in high yield with excellent enantiomeric excess. The obtained conjugate addition products were readily converted to synthetically useful and important chiral building blocks.

  DOI：

  10.1021/ja307668b

文献信息

• JP5749548
  申请人：——

  公开号：——

  公开（公告）日：——
• Powerful Amino Diol Catalyst for Effecting the Direct Asymmetric Conjugate Addition of Aldehydes to Acrylates
  作者：Taichi Kano、Fumitaka Shirozu、Matsujiro Akakura、Keiji Maruoka

  DOI：10.1021/ja307668b

  日期：2012.9.26

  Di-tert-butyl methylenemalonate (1) could be employed as a reactive equivalent of a three-carbon Michael acceptor such as acrylate in a direct asymmetric conjugate addition of aldehydes catalyzed by an axially chiral amino diol (S)-3a. Furthermore, acrylate, an unexplored and challenging substrate in enamine catalysis, has also been successfully employed in asymmetric conjugate addition reaction. Relatively inert acrylate is doubly activated by polyfluoroalkyl group of 2 and the hydroxyl group on the axially chiral amino diol catalyst (S)-3b, giving corresponding conjugate adducts in high yield with excellent enantiomeric excess. The obtained conjugate addition products were readily converted to synthetically useful and important chiral building blocks.