(E)-(2S,3R)-3-Hydroxy-2-methyl-5-phenyl-pent-4-enoic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-(2S,3R)-3-Hydroxy-2-methyl-5-phenyl-pent-4-enoic acid ethyl ester
• 英文别名: ethyl (E,2S,3R)-3-hydroxy-2-methyl-5-phenylpent-4-enoate
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: ABILMTYZOJXHJM-IMYBMRPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 2-methyl-3-oxo-5-phenylpent-4-enoate 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 (2S,3S,E)-ethyl 3-hydroxy-2-methyl-5-phenylpent-4-enoate 、 (E)-(2S,3R)-3-Hydroxy-2-methyl-5-phenyl-pent-4-enoic acid ethyl ester
  参考文献：
  名称：

  氯化锰（II）或四丁基硼氢化铵催化的硼氢化钠立体选择性还原2-甲基-3-氧代酯（或酰胺）。实用的赤型和苏型-3-羟基-2-甲基酯（或酰胺）的制备方法

  摘要：

  赤-3-羟基-2- methylpropionates或赤-3-羟基-2-甲基丙酰胺用高立体选择性加入NaBH制备4减少在相应的2-甲基-3-氧代酯或2-甲基-3-氧代酰胺的催化量的氯化锰（II）的存在。另一方面，用n -Bu 4 NBH 4还原这些底物选择性地提供了苏式异构体。还描述了在1N HCl-MeOH中用NaBH 3 CN对2-甲基-3-氧代酰胺的赤型选择性还原。

  DOI：

  10.1016/s0040-4020(01)81804-4

文献信息

• A facile preparation of indium enolates and their Reformatsky- and Darzens-type reactions
  作者：Tsunehisa Hirashita、Kenji Kinoshita、Hatsuo Yamamura、Masao Kawai、Shuki Araki

  DOI：10.1039/a907334e

  日期：——

  Indium enolates were readily prepared by transmetalation of lithium enolates with indium trichloride, and were subsequently reacted with aldehydes to give β-hydroxy esters in high yields. Indium α-bromo enolates were also prepared and reacted with carbonyl compounds to give Darzens-type α,β-epoxy carbonyl products.

  铟烯醇盐通过锂烯醇盐与三氯化铟的金属交换反应容易制备，随后与醛反应生成高产率的β-羟基酯。铟α-溴烯醇盐也被制备并与羰基化合物反应，生成Darzens 型α,β-环氧羰基产物。
• Asymmetric Aldol Reaction with Diisopinocampheyl Enolborinates of Propionates
  作者：P. Veeraraghavan Ramachandran、Debarshi Pratihar

  DOI：10.1021/ol802850w

  日期：2009.4.2

  A convenient and general, reagent-controlled, diastereo- and enantioselective aldol reaction of diisopinocampheylboron enolates of esters, followed by reduction, has been developed as an alternative to crotylboration-ozonolysis. This protocol was then exploited for the double diastereoselective synthesis of the C11-C17 subunit of (-)-dictyostatin.
• Stereoselective reduction of 2-methyl-3-oxo esters (or amides) with sodium borohydride catalyzed by manganese(II) chloride or tetrabutylammonium borohydride. A practical preparation of erythro and threo-3-hydroxy-2-methyl esters (or amides)
  作者：Masahiko Taniguchi、Hideaki Fujii、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/s0040-4020(01)81804-4

  日期：1993.1

  lpropionamides were prepared with high stereoselectivity by NaBH4 reduction of the corresponding 2-methyl-3-oxo esters or 2-methyl-3-oxo amides in the presence of a catalytic amount of manganese(II) chloride. On the other hand, reduction of these substrates with n-Bu4NBH4 provided threo-isomers selectively. erythro-Selective reduction of 2-methyl-3-oxo amides with NaBH3CN in 1N HCl-MeOH is also described

  赤-3-羟基-2- methylpropionates或赤-3-羟基-2-甲基丙酰胺用高立体选择性加入NaBH制备4减少在相应的2-甲基-3-氧代酯或2-甲基-3-氧代酰胺的催化量的氯化锰（II）的存在。另一方面，用n -Bu 4 NBH 4还原这些底物选择性地提供了苏式异构体。还描述了在1N HCl-MeOH中用NaBH 3 CN对2-甲基-3-氧代酰胺的赤型选择性还原。