methyl (±)-anti-2-iodo-3-methoxy-3-phenylpropanoate | 93643-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (±)-anti-2-iodo-3-methoxy-3-phenylpropanoate
• 英文别名: methyl 2-iodo-3-methoxy-3-phenylpropanoate；erythro-2-Iod-3-methoxy-3-phenyl-propionsaeure-methylester；methyl (2S,3S)-2-iodo-3-methoxy-3-phenylpropanoate
• CAS: 93643-71-1；131846-31-6；133379-84-7
• 化学式: C₁₁H₁₃IO₃
• 分子量: 320.127
• InChiKey: VQJYSFXRQXVGNP-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (±)-anti-2-iodo-3-methoxy-3-phenylpropanoate 在 lithium iodide 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3S)-2-Iodo-3-methoxy-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Stereoselective Radical Carbon−Carbon Bond Forming Reactions of β-Alkoxy Esters:  Atom and Group Transfer Allylations under Bidentate Chelation Controlled Conditions

  摘要：

  The radical allylation of a series of beta-alkoxy esters using allyltrimethylsilane in the presence of MgBr2 . OEt(2) is described. Under bidentate chelation-controlled conditions, allyltrimethylsilane rivals allyltributyltin in efficiency and is a superior reagent from ecological and practical perspectives. The reactions work with iodides and bromides as well as phenylselenides. The isolation of gamma-phenylseleno intermediates indicates that the reaction proceeds by an atom transfer process. These reactions require initiation with Et(3)B and can be inhibited by galvinoxyl, m- and p-dinitrobenzene indicating that this atom transfer sequence involves the intermediacy of radicals.

  DOI：

  10.1021/ja9541241
• 作为产物：
  描述：

  甲醇 、 Methyl cinnamate 生成 methyl (±)-anti-2-iodo-3-methoxy-3-phenylpropanoate
  参考文献：
  名称：

  Banerji, Avijit; Ghosal, Tapasree, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 5, p. 427 - 430

  摘要：

  DOI：

文献信息

• Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents
  作者：Manoj K. Agrawal、Subbarayappa Adimurthy、Bishwajit Ganguly、Pushpito K. Ghosh

  DOI：10.1016/j.tet.2009.01.095

  日期：2009.4

  halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br−/BrO3− and I−/IO3− reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br−/BrO3− and I−/IO3−, respectively. Of the two reagents, I−/IO3− was established to be the preferred reagent for vicinal functionalization of linear alkenes and

  比较评价在邻位卤代醇，卤代甲基醚和卤代乙酸盐的合成由从使用2-烯烃：1溴- /的BrO 3 -和我- / IO 3 -试剂。在许多情况下，两种试剂都以高收率选择性地提供产物。得到最高卤素原子效率为97％和溴93％- /的BrO 3 -和我- / IO 3 - ，分别。这两个试剂，我- / IO 3 -已确定“丙烯酰胺”是用于直链烯烃的邻位官能化以及用于制备卤代乙酸酯的优选试剂。然而，只有溴- /的BrO 3 -是有效的邻位官能反式-二苯乙烯和查耳酮。
• Stereoselective rardical-mediated reduction and alkylation of α-halo esters
  作者：Y. Guindon、J.-F. Lavallée、L. Boisvert、C. Chabot、D. Delorme、C. Yoakim、D. Hall、R. Lemieux、B. Simoneau

  DOI：10.1016/s0040-4039(00)71209-3

  日期：1991.1

  Radical-mediated reduction and alkylation of β-alkoxy-α-halo esters could be achieved with good stereoselection at low temperature.

  在低温下以良好的立体选择可以实现β-烷氧基-α-卤代酯的自由基介导的还原和烷基化。
• Vishwakarma,L.C.; Walia,J.S., Journal of the Indian Chemical Society, 1976, vol. 53, p. 156 - 162
  作者：Vishwakarma,L.C.、Walia,J.S.

  DOI：——

  日期：——
• Banerji, Avijit; Ghosal, Tapasree, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 5, p. 427 - 430
  作者：Banerji, Avijit、Ghosal, Tapasree

  DOI：——

  日期：——
• Stereoselective Radical Carbon−Carbon Bond Forming Reactions of β-Alkoxy Esters:  Atom and Group Transfer Allylations under Bidentate Chelation Controlled Conditions
  作者：Y. Guindon、B. Guérin、C. Chabot、W. Ogilvie

  DOI：10.1021/ja9541241

  日期：1996.1.1

  The radical allylation of a series of beta-alkoxy esters using allyltrimethylsilane in the presence of MgBr2 . OEt(2) is described. Under bidentate chelation-controlled conditions, allyltrimethylsilane rivals allyltributyltin in efficiency and is a superior reagent from ecological and practical perspectives. The reactions work with iodides and bromides as well as phenylselenides. The isolation of gamma-phenylseleno intermediates indicates that the reaction proceeds by an atom transfer process. These reactions require initiation with Et(3)B and can be inhibited by galvinoxyl, m- and p-dinitrobenzene indicating that this atom transfer sequence involves the intermediacy of radicals.