[(2S,4S)-4-(2-methylphenoxy)pentan-2-yl] 2-diazoacetate | 1373521-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(2S,4S)-4-(2-methylphenoxy)pentan-2-yl] 2-diazoacetate
• CAS: 1373521-67-5
• 化学式: C₁₄H₁₈N₂O₃
• 分子量: 262.309
• InChiKey: XTKQGEGVDORGCR-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2S,4S)-4-(2-methylphenoxy)pentan-2-yl] 2-diazoacetate 在 [Rh2(O2CCPh3)4] 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到(3S,5S,8R)-3,5,13-trimethyl-2,6-dioxabicyclo[6.5.0]trideca-1(13),9,11-trien-7-one
  参考文献：
  名称：

  Remote stereocontrol of intramolecular rhodium carbene addition driven by a small and flexible chiral 2,4-pentanediol tether

  摘要：

  Intramolecular rhodium carbenoid additions were studied using 2,4-pentanidiol as a chiral tether between a diazo group, a precursor of the carbene, and an aromatic group to be reacted with the carbene. The reaction was designed to perform the addition at a remote position, conserving the original high stereoselectivity appeared at additions near the tether, in addition to high regioselectivity and sufficient reaction efficiency. Substitution on the near reaction sites, the carbene carbon and aromatic group, in the reactant was effective to relegate the reaction site to a remote position. In the present study, two remote reactions, one dealing with C-H insertion and the other classified in Buchner reaction, were found to give sole products in high yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.009
• 作为产物：
  描述：

  在 4-乙酰氨基苯磺酰叠氮 、 三乙胺 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 44.0h， 以75%的产率得到[(2S,4S)-4-(2-methylphenoxy)pentan-2-yl] 2-diazoacetate
  参考文献：
  名称：

  Remote stereocontrol of intramolecular rhodium carbene addition driven by a small and flexible chiral 2,4-pentanediol tether

  摘要：

  Intramolecular rhodium carbenoid additions were studied using 2,4-pentanidiol as a chiral tether between a diazo group, a precursor of the carbene, and an aromatic group to be reacted with the carbene. The reaction was designed to perform the addition at a remote position, conserving the original high stereoselectivity appeared at additions near the tether, in addition to high regioselectivity and sufficient reaction efficiency. Substitution on the near reaction sites, the carbene carbon and aromatic group, in the reactant was effective to relegate the reaction site to a remote position. In the present study, two remote reactions, one dealing with C-H insertion and the other classified in Buchner reaction, were found to give sole products in high yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.009

文献信息

• Remote stereocontrol of intramolecular rhodium carbene addition driven by a small and flexible chiral 2,4-pentanediol tether
  作者：Chun Young Im、Takashi Sugimura

  DOI：10.1016/j.tet.2012.03.009

  日期：2012.5

  Intramolecular rhodium carbenoid additions were studied using 2,4-pentanidiol as a chiral tether between a diazo group, a precursor of the carbene, and an aromatic group to be reacted with the carbene. The reaction was designed to perform the addition at a remote position, conserving the original high stereoselectivity appeared at additions near the tether, in addition to high regioselectivity and sufficient reaction efficiency. Substitution on the near reaction sites, the carbene carbon and aromatic group, in the reactant was effective to relegate the reaction site to a remote position. In the present study, two remote reactions, one dealing with C-H insertion and the other classified in Buchner reaction, were found to give sole products in high yields. (C) 2012 Elsevier Ltd. All rights reserved.