2-cyclooctenyl p-nitrobenzoate | 100956-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-cyclooctenyl p-nitrobenzoate
• 英文别名: (Z)-cyclooct-2-en-1-yl 4-nitrobenzoate；(+/-)-4-nitro-benzoic acid cyclooct-2c-enyl ester；(+/-)-4-Nitro-benzoesaeure-cyclooct-2c-enylester；[(2Z)-cyclooct-2-en-1-yl] 4-nitrobenzoate
• CAS: 100956-53-4
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: XDRNSOJKKJUDTM-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  顺-环辛烯 、 tert-butyl 4-nitrobenzoperoxoate 在 copper(I) bromide 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以43%的产率得到2-cyclooctenyl p-nitrobenzoate
  参考文献：
  名称：

  Catalytic enantioselective allylic oxidation of olefins with copper(I) catalysts and new perester oxidants

  摘要：

  Asymmetric allylic oxidation of cyclic olefins using a catalytic amount of copper(I) bisoxazoline complexes and new peresters was investigated to give allylic benzoate esters in high selectivity (similar to 80%ee), yield (70-80%), and at reasonable rates (5-7 d) at -20 degrees C in acetonitrile. Cyclohexene reacted with pam-chloro tert-butylperbenzoate and 15 mol% diphenylbisoxazoline-copper(I) hexafluorophosphate to give benzoate product in 83% yield and 75% ee. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01011-9

文献信息

• Effects of Silver Carbonate and <i>p</i>-Nitrobenzoic Acid for Accelerating Palladium-Catalyzed Allylic C–H Acyloxylation
  作者：Aymen Skhiri、Haruki Nagae、Hayato Tsurugi、Masahiko Seki、Kazushi Mashima

  DOI：10.1021/acs.orglett.1c02406

  日期：2021.9.17

  An allylic C–H acyloxylation of terminal alkenes with 4-nitrobenzoic acid was assisted by a bidentate-sulfoxide-ligated palladium catalyst combined with 1,4-benzoquinone and Ag2CO3 under mild reaction conditions. The catalytic activity was remarkably enhanced by Ag2CO3 as an additive and 4-nitrobenzoic acid as a carboxylate source; both components were essential to exhibiting high catalytic activity

  在温和的反应条件下，末端烯烃与 4-硝基苯甲酸的烯丙基 C-H 酰氧基化反应由双齿亚砜连接的钯催化剂与 1,4-苯醌和 Ag 2 CO 3组合辅助。Ag 2 CO 3作为添加剂和4-硝基苯甲酸作为羧酸盐源显着提高了催化活性；这两种组分对于表现出高催化活性、高支链选择性和钯催化剂负载量低的宽底物范围都是必不可少的。7-辛烯酸乙酯 ( 1a ) 的支链选择性烯丙基酰氧基化得到产物 6,8-二羟基辛酸乙酯 ( 5 )，这是一种有用的合成中间体 ( R)-α-硫辛酸。
• Catalytic enantioselective allylic oxidation of olefins with copper(I) catalysts and new perester oxidants
  作者：Merritt B. Andrus、Xi Chen

  DOI：10.1016/s0040-4020(97)01011-9

  日期：1997.12

  Asymmetric allylic oxidation of cyclic olefins using a catalytic amount of copper(I) bisoxazoline complexes and new peresters was investigated to give allylic benzoate esters in high selectivity (similar to 80%ee), yield (70-80%), and at reasonable rates (5-7 d) at -20 degrees C in acetonitrile. Cyclohexene reacted with pam-chloro tert-butylperbenzoate and 15 mol% diphenylbisoxazoline-copper(I) hexafluorophosphate to give benzoate product in 83% yield and 75% ee. (C) 1997 Elsevier Science Ltd.