(2RS,3S,6R)-tetrahydro-3-(N-1-naphthyl)carbamoyloxy-6-ethenyl-2-phenylselenylmethyl-2,6-dimethyl-2H-pyuran | 252857-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2RS,3S,6R)-tetrahydro-3-(N-1-naphthyl)carbamoyloxy-6-ethenyl-2-phenylselenylmethyl-2,6-dimethyl-2H-pyuran
• 英文别名: [(3S,6R)-6-ethenyl-2,6-dimethyl-2-(phenylselanylmethyl)oxan-3-yl] N-naphthalen-1-ylcarbamate
• CAS: 252857-36-6
• 化学式: C₂₇H₂₉NO₃Se
• 分子量: 494.492
• InChiKey: CRZDIHJJOITGKR-OGUPFJCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2RS,3S,6R)-tetrahydro-3-(N-1-naphthyl)carbamoyloxy-6-ethenyl-2-phenylselenylmethyl-2,6-dimethyl-2H-pyuran 在 甲醇 、 三苯基氢化锡 、 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 26.0h， 生成 2H-吡喃-3-醇,6-乙烯基四氢-2,2,6-三甲基-,(3S,6R)-
  参考文献：
  名称：

  Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route

  摘要：

  Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation of (R)- or (S)-linalyl acetate with AD-mix-alpha or AD-mix-beta, followed by a completely stereoselective N-phenylselenophthalimide cyclization of an intermediate allylic alcohol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00359-6
• 作为产物：
  描述：

  (3S/R,6R)-6-acetoxy-2,6-dimethyloct-7-en-2,3-diol 在 吡啶 、 甲醇 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 (2RS,3S,6R)-tetrahydro-3-(N-1-naphthyl)carbamoyloxy-6-ethenyl-2-phenylselenylmethyl-2,6-dimethyl-2H-pyuran
  参考文献：
  名称：

  Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route

  摘要：

  Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation of (R)- or (S)-linalyl acetate with AD-mix-alpha or AD-mix-beta, followed by a completely stereoselective N-phenylselenophthalimide cyclization of an intermediate allylic alcohol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00359-6

文献信息

• Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route
  作者：Giovanni Vidari、Anna Di Rosa、Giuseppe Zanoni、Carlo Bicchi

  DOI：10.1016/s0957-4166(99)00359-6

  日期：1999.9

  Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation of (R)- or (S)-linalyl acetate with AD-mix-alpha or AD-mix-beta, followed by a completely stereoselective N-phenylselenophthalimide cyclization of an intermediate allylic alcohol. (C) 1999 Elsevier Science Ltd. All rights reserved.