methyl 1-(2-thienyl)-2-propenyl carbonate | 87802-73-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: methyl 1-(2-thienyl)-2-propenyl carbonate
• 英文别名: methyl 1-thiophen-2-ylprop-2-enyl carbonate
• CAS: 87802-73-1
• 化学式: C₉H₁₀O₃S
• 分子量: 198.243
• InChiKey: NCIACBIBGMLGTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-(2-thienyl)-2-propenyl carbonate 、 sodium dimethyl malonate 以70%的产率得到
  参考文献：
  名称：

  TROST, B. M.;HUNG, MING-HONG, J. AMER. CHEM. SOC., 1983, 105, N 26, 7757-7759

  摘要：

  DOI：

文献信息

• Catalytic compositions and methods for asymmetric allylic alkylation
  申请人：——

  公开号：US20020198383A1

  公开（公告）日：2002-12-26

  Complexes of a selected class of chiral ligands with molybdenum, tungsten or chromium, preferably molybdenum, are effective as catalysts in highly enantioselective and regioselective alkylation of allylic substrates.

  一种选择性手性配体与钼、钨或铬形成的络合物，优选钼，可作为催化剂，在烯丙基底物的高对映选择性和区域选择性烷基化反应中具有高效性。
• Iridium Complex-Catalyzed Allylic Amination of Allylic Esters
  作者：Ryo Takeuchi、Naoki Ue、Keisuke Tanabe、Kengo Yamashita、Norihito Shiga

  DOI：10.1021/ja0112036

  日期：2001.10.1

  Iridium complex-catalyzed allylic amination of allylic carbonates was studied. The solvent strongly affected the catalytic activity. The use of a polar solvent such as EtOH is essential for obtaining the products in high yield, The reaction of (E)-3-substituted-2-propenyl carbonate and 1-substituted-2-propenyl carbonate with pyrrolidine in the presence of a catalytic amount of [Ir(COD)Cl](2) and P(OPh)(3) (P/Ir = 2) gave a branch amine with up to 99% selectivity. Both secondary and primary amines could be used for this reaction. When a primary amine was used, selective monoallylation occurred. No diallylation product was obtained. The reaction of 1,1-disubstituted-2 propenyl acetate with amines exclusively gave an alpha,alpha -disubstituted allylic amine. This reaction provides an alternative route to the addition of an organometallic reagent to ketimines. for the preparation of such amines. The reaction of (Z)-3-substituted-2-propenyl carbonate with amines gave (Z)-linear amines with up to 100% selectivity. In all cases, no (E)-linear amine was obtained. The selectivities described here have not been achieved in similar palladium complex-catalyzed reactions.
• Tungsten-catalyzed allylic alkylations. New avenues for selectivity
  作者：Barry M. Trost、Ming Hong Hung

  DOI：10.1021/ja00364a055

  日期：1983.12
• Asymmetric Molybdenum-Catalyzed Alkylations
  作者：Barry M. Trost、Iwao Hachiya

  DOI：10.1021/ja973298a

  日期：1998.2.1
• Asymmetric molybdenum(0)-catalyzed allylic substitution
  作者：Andrei V. Malkov、Paul Spoor、Victoria Vinader、Pavel Kočovský

  DOI：10.1016/s0040-4039(00)02007-4

  日期：2001.1

  Application of new ligands (R)-(-)-8, (S)-(+)-16, and (S)-(+)-17 to the title reaction (1 or 2 -> 3) led to excellent regio-and enantioselectivities (> 30:1; less than or equal to 98% ee); although lacking the C-2-symmetry, the catalysts can be viewed as quasi-C-2-symmetrical since the single chiral center is sufficient to determine the sense of wrapping of the metal by the ligand. (C) 2001 Published by Elsevier Science Ltd.