{2-[(2-hydroxy-6-oxo-cyclohex-1-enyl)-(6-nitro-benzo[1,3]dioxol-5-yl)-methylsulfanyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester | 851935-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: {2-[(2-hydroxy-6-oxo-cyclohex-1-enyl)-(6-nitro-benzo[1,3]dioxol-5-yl)-methylsulfanyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 9H-fluoren-9-ylmethyl N-[2-[(2-hydroxy-6-oxocyclohexen-1-yl)-(6-nitro-1,3-benzodioxol-5-yl)methyl]sulfanylethyl]carbamate
• CAS: 851935-62-1
• 化学式: C₃₁H₂₈N₂O₈S
• 分子量: 588.638
• InChiKey: RGDHNONWSFPQOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  {2-[(2-hydroxy-6-oxo-cyclohex-1-enyl)-(6-nitro-benzo[1,3]dioxol-5-yl)-methylsulfanyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 以 氘代氯仿 为溶剂， 生成 2-(6-Nitro-benzo[1,3]dioxol-5-ylmethylene)-cyclohexane-1,3-dione
  参考文献：
  名称：

  A Three-Component Photoreversible Tag for Thiols

  摘要：

  A one-pot coupling of a 1,3-diketone, an aldehyde, and an alkanethiol has been developed to produce a protected sulfide. Through use of an o-nitrophenylbenzaldehyde, this method provides a one-step route to a photochemically reversible thiol-protecting group. The kinetics of photolysis were established using H-1 NMR analysis, which allows for the rate to be based on the entire reaction scheme.

  DOI：

  10.1021/jo0481396
• 作为产物：
  描述：

  N-9-fluorenylmethyloxycarbonyl-2-aminoethane thiol 、 6-硝基胡椒醛 、 1,3-环己二酮 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以66%的产率得到{2-[(2-hydroxy-6-oxo-cyclohex-1-enyl)-(6-nitro-benzo[1,3]dioxol-5-yl)-methylsulfanyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  A Three-Component Photoreversible Tag for Thiols

  摘要：

  A one-pot coupling of a 1,3-diketone, an aldehyde, and an alkanethiol has been developed to produce a protected sulfide. Through use of an o-nitrophenylbenzaldehyde, this method provides a one-step route to a photochemically reversible thiol-protecting group. The kinetics of photolysis were established using H-1 NMR analysis, which allows for the rate to be based on the entire reaction scheme.

  DOI：

  10.1021/jo0481396

文献信息

• A Three-Component Photoreversible Tag for Thiols
  作者：Kristine M. Clarke、James J. La Clair、Michael D. Burkart

  DOI：10.1021/jo0481396

  日期：2005.4.1

  A one-pot coupling of a 1,3-diketone, an aldehyde, and an alkanethiol has been developed to produce a protected sulfide. Through use of an o-nitrophenylbenzaldehyde, this method provides a one-step route to a photochemically reversible thiol-protecting group. The kinetics of photolysis were established using H-1 NMR analysis, which allows for the rate to be based on the entire reaction scheme.