(2RS,3RS)-2-allyl-3-methylcyclohexanone | 61674-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2RS,3RS)-2-allyl-3-methylcyclohexanone
• 英文别名: trans-3-Methyl-2-(2-propenyl)cyclohexanone；trans-2-allyl-3-methylcyclohexanone；(2S,3R)-3-methyl-2-prop-2-enylcyclohexan-1-one
• CAS: 61674-94-0
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: JNDGVJUNFDJOLD-BDAKNGLRSA-N

物化性质

• 沸点：
  210.2±9.0 °C(Predicted)
• 密度：
  0.884±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2RS,3RS)-2-allyl-3-methylcyclohexanone 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 57.5h， 生成 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-(2Z)-(but-2-enoyloxy)pentanoate
  参考文献：
  名称：

  模仿Aplysiatoxin药理团的大环二内酯的合成与构象分析

  摘要：

  少数类型的大环双内酯的3，即，9，10，11，和外延11，其包括3,4-二羟基戊酸单元，aplysiatoxin的药效，和构象预组织ω -hydroxynonanoic羧酸单元合成。这些大双内酯的二羟基戊酰基部分的构象分析（基于2 J和3 J NMR耦合常数）表明，通过在ω-羟基壬酸部分中实现的立体异构中心，整个大双内酯环发生构象诱导的程度。

  DOI：

  10.1002/hlca.200390151
• 作为产物：
  描述：

  2-(丙-2-烯基)环己-2-烯-1-酮 、 甲基锂 在 copper(l) iodide 、 水杨酸甲酯 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以80%的产率得到(2RS,3RS)-2-allyl-3-methylcyclohexanone
  参考文献：
  名称：

  模仿Aplysiatoxin药理团的大环二内酯的合成与构象分析

  摘要：

  少数类型的大环双内酯的3，即，9，10，11，和外延11，其包括3,4-二羟基戊酸单元，aplysiatoxin的药效，和构象预组织ω -hydroxynonanoic羧酸单元合成。这些大双内酯的二羟基戊酰基部分的构象分析（基于2 J和3 J NMR耦合常数）表明，通过在ω-羟基壬酸部分中实现的立体异构中心，整个大双内酯环发生构象诱导的程度。

  DOI：

  10.1002/hlca.200390151

文献信息

• The asymmetric synthesis of (−)-pumiliotoxin C using tandem catalysis
  作者：Ewold W. Dijk、Lavinia Panella、Pedro Pinho、Robert Naasz、Auke Meetsma、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1016/j.tet.2004.06.148

  日期：2004.10

  The potent neurotoxin (-)-pumiliotoxin C has been prepared in 8 steps starting from 2-cyclohexenone. Key steps are a tandem asymmetric conjugate addition-allylic substitution reaction and a tandem Heck-allylic substitution reaction. (C) 2004 Elsevier Ltd. All rights reserved.
• Radical .alpha.-allylation of alkyl-substituted .alpha.-(phenylseleno)cycloalkanones
  作者：Takeshi Toru、Tatsuya Okumura、Yoshio Ueno

  DOI：10.1021/jo00291a033

  日期：1990.2
• Methods
  申请人：Sattentau James Quentin

  公开号：US20070110759A1

  公开（公告）日：2007-05-17

  The presence of aldehydic groups on proteins and lipoproteins is associated with various pathological conditions such as atherosclerosis, diabetes and alcoholic liver disease. Respiratory syncytial virus (RSV) is a major cause of severe respiratory disease in infants and the elderly. RSV vaccine research has been impeded because a formalin-inactivated vaccine used in the 1960s predisposed infants to enhanced disease following subsequent natural infection. The molecular basis for the vaccine-induced hypersensitivity has not, however, been elucidated. We show here that addition of reactive carbonyl groups to ovalbumin (OVA) by treatment with glycolaldehyde or formaldehyde increases the protein's immunogenicity in mice, and biases the immune response towards a Th2-type response. The increased immunogenicity and the Th2-type response can both be abrogated by reductive elimination of the reactive carbonyl groups. We demonstrate that RSV inactivated by formaldehyde (FI-RSV), following a protocol used previously to prepare the vaccine, contains reactive carbonyl groups. Using a well-established model of FI-RSV vaccine-induced pathology, immunisation of mice with FI-RSV and subsequent challenge of the mice with live RSV induced Th2-type responses, lung eosinophilia and weight loss that were abrogated by reductive elimination of the reactive carbonyl groups. We thus propose that the addition of reactive carbonyl groups to RSV during inactivation is the major mechanism that drives the Th2-immune response and associated pathology. Moreover, we suggest that the addition of reactive carbonyl groups to other antigens, including vaccines, may be responsible for other hypersensitive and allergic reactions described in the literature.