cinnamate de methyle β-deutere | 60975-76-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: cinnamate de methyle β-deutere
• 英文别名: (E)-3-deuterio-3-phenyl-acrylic acid methyl ester；trans-3-Deuterio-zimtsaeuremethylester；methyl (E)-3-deuterio-3-phenylprop-2-enoate
• CAS: 60975-76-0
• 化学式: C₁₀H₁₀O₂
• 分子量: 163.18
• InChiKey: CCRCUPLGCSFEDV-HZOGUMOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  苯甲醛 、 甲基吡咯烷-2-羧酸 、 cinnamate de methyle β-deutere 生成 dimethyl (1R,2S,3R,8R)-1-deuterio-1,3-diphenyl-3,5,6,7-tetrahydro-2H-pyrrolizine-2,8-dicarboxylate
  参考文献：
  名称：

  JOUCLA, MARC;MORTIER, JACQUES;HAMELIN, JACK;TOUPET, LOIC, BULL. SOC. CHIM. FR.,(1988) N 1, 143-150

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (2Z)-3-phenylprop-2-enoate 在 palladium on activated charcoal deuterated formic acid 、 三乙胺 作用下， 反应 1.0h， 生成 methyl (α-deuterio)cinnamate 、 cinnamate de methyle β-deutere
  参考文献：
  名称：

  Evidence for Direct Hydride Delivery from Formic Acid in Transfer Hydrogenation

  摘要：

  The regioselectivity of hydrometalation in transfer hydrogenation was investigated by tracing the fate of the deuterium label in both the formyl and carboxyl positions of formic acid during the isomerization of a cis enol ether. The deuterium from the formyl position is incorporated exclusively into the electron-deficient center of the double bond; this indicates that hydride attack occurs during transfer hydrogenation. The fact that the formyl hydrogen is more reactive than the carboxyl hydrogen suggests that the identities of the two hydrogens are not scrambled during transfer hydrogenation. We propose that the delivery of the formyl hydrogen atom is concerted with decarboxylation rather than proceeding through the formation of a metal dihydrido species.

  DOI：

  10.1002/(sici)1521-3765(19990802)5:8<2237::aid-chem2237>3.0.co;2-o

文献信息

• Joucla, Marc; Mortier, Jacques; Hamelin, Jack, Bulletin de la Societe Chimique de France, 1988, # 1, p. 143 - 150
  作者：Joucla, Marc、Mortier, Jacques、Hamelin, Jack、Toupet, Loic

  DOI：——

  日期：——
• JOUCLA, MARC;MORTIER, JACQUES;HAMELIN, JACK;TOUPET, LOIC, BULL. SOC. CHIM. FR.,(1988) N 1, 143-150
  作者：JOUCLA, MARC、MORTIER, JACQUES、HAMELIN, JACK、TOUPET, LOIC

  DOI：——

  日期：——
• Evidence for Direct Hydride Delivery from Formic Acid in Transfer Hydrogenation
  作者：Jinquan Yu、Jonathan B. Spencer

  DOI：10.1002/(sici)1521-3765(19990802)5:8<2237::aid-chem2237>3.0.co;2-o

  日期：1999.8.2

  The regioselectivity of hydrometalation in transfer hydrogenation was investigated by tracing the fate of the deuterium label in both the formyl and carboxyl positions of formic acid during the isomerization of a cis enol ether. The deuterium from the formyl position is incorporated exclusively into the electron-deficient center of the double bond; this indicates that hydride attack occurs during transfer hydrogenation. The fact that the formyl hydrogen is more reactive than the carboxyl hydrogen suggests that the identities of the two hydrogens are not scrambled during transfer hydrogenation. We propose that the delivery of the formyl hydrogen atom is concerted with decarboxylation rather than proceeding through the formation of a metal dihydrido species.