3-(2-(4-iodophenyl)-2-oxoethyl)isobenzofuran-1(3H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-(4-iodophenyl)-2-oxoethyl)isobenzofuran-1(3H)-one
• 英文别名: (R)-3-(2-(4-iodophenyl)-2-oxoethyl)isobenzofuran-1(3H)-one；(3R)-3-[2-(4-iodophenyl)-2-oxoethyl]-3H-2-benzofuran-1-one
• 化学式: C₁₆H₁₁IO₃
• 分子量: 378.166
• InChiKey: MQRJYJUXRWQMCD-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  dimethyl ((1S,3R)-3-(2-(4-iodophenyl)-2-oxoethyl)-1,3-dihydroisobenzofuran-1-yl)phosphonate 在 丙酮 作用下， 反应 62.0h， 以39%的产率得到3-(2-(4-iodophenyl)-2-oxoethyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Organocatalytic, Chemoselective Hydrophosphenylation/oxa-Michael Addition Cascade toward Diastereo- and Enantioenriched 1,3-Dihydroisobenzofuryl Phosphonates

  摘要：

  An efficient method for the construction of chiral C-P bond via an enantioselective 1,2-hydrophosphenylation followed by an oxa-Michael addition cascade of ortho-formyl chalcones has been developed. This provides the diastereoenriched (cis)-1,3-dihydroisobenzofuryl phosphonates with excellent enantioselectivities (up to >99%). The origin of enantio- and diastereoselectivity is induced by using a chiral bifunctional organocatalyst. Further, functionalization to highly enantioselective 3-substituted phthalides has also been demonstrated.

  DOI：

  10.1021/acs.joc.8b01048

文献信息

• Catalytic Asymmetric Conjugate Addition of Carboxylic Acids via Oxa-Michael Reaction of Peroxy Hemiacetals followed by Kornblum DeLaMare Fragmentation
  作者：Biswajit Parhi、Sanjay Maity、Prasanta Ghorai

  DOI：10.1021/acs.orglett.6b02463

  日期：2016.10.21

  Disclosed herein an overall methodology constitutes an equivalent to the long sought after enantioselective intramolecular oxa-Michael (IOM) reaction of carboxylic acids. An organocatalyzed IOM reaction of in situ formed peroxy hemiacetals followed by a Kornblum DeLaMare type rearrangement cascade provides a broad class of chiral lactones in good yields and with excellent enatioselectvities. Remarkably

  本文公开了一种总体方法，其等同于对羧酸的对映选择性分子内氧杂-迈克尔（IOM）反应的长期追求。原位形成的过氧半缩醛的有机催化IOM反应，然后进行Kornblum DeLaMare型重排级联反应，可以提供大量的手性内酯，收率高，对映选择性高。值得注意的是，无需任何硅胶柱色谱即可获得纯手性内酯，并且在许多情况下，通过简单的己烷洗涤分离的固体产物，进一步提高了对映选择性。