2,2,3-trimethyl-3-(2,5-dimethoxy-4-methylphenyl)cyclopentan-1-one | 243117-90-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,2,3-trimethyl-3-(2,5-dimethoxy-4-methylphenyl)cyclopentan-1-one
• 英文别名: (+/-)-3-(2,5-dimethoxy-4-methylphenyl)-2,2,3-trimethylcyclopentanone；Cyclopentanone, 3-(2,5-dimethoxy-4-methylphenyl)-2,2,3-trimethyl-；3-(2,5-dimethoxy-4-methylphenyl)-2,2,3-trimethylcyclopentan-1-one
• CAS: 243117-90-0
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: UISXRNSZEJCKDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,3-trimethyl-3-(2,5-dimethoxy-4-methylphenyl)cyclopentan-1-one 在 盐酸肼 、 三溴化硼 、 一水合肼 作用下， 以 二氯甲烷 、 二乙二醇 为溶剂， 反应 5.0h， 生成 4-methoxy-5-methyl-2-(1,2,2-trimethylcyclopentyl)phenol
  参考文献：
  名称：

  Pal, Ashutosh; Gupta, Pranab Dutta; Mukherjee, Debabrata, Journal of the Indian Chemical Society, 2003, vol. 80, # 11, p. 989 - 995

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl 2,2,3-trimethyl-3-(2,5-dimethoxy-4-methylphenyl)adipate 在 potassium tert-butylate 、 二甲基亚砜 、 sodium chloride 作用下， 以 苯 为溶剂， 生成 2,2,3-trimethyl-3-(2,5-dimethoxy-4-methylphenyl)cyclopentan-1-one
  参考文献：
  名称：

  轻松进行涉及受阻酯烷基化的（±）-α-香薄荷醇，（±）-α-cuparenone和（±）-HM-1甲醚的全合成

  摘要：

  （±）-α-herbertenol的全合成1，（±）-α-cuparenone 4和（±）-HM-1甲基醚3已成功地完成涉及酯的α，α-二甲基化8A，17和图8b分别作为关键步骤。

  DOI：

  10.1016/s0040-4039(99)00835-7

文献信息

• Palladium (II) catalyzed 5-endo epoxynitrile cyclizations: total syntheses of enokipodins A and B
  作者：Jesús Armando Luján-Montelongo、José G. Ávila-Zárraga

  DOI：10.1016/j.tetlet.2010.02.072

  日期：2010.4

  New total syntheses of the cuparenic sesquiterpenes enokipodins A and B were accomplished. The key step involves a novel, cationic-controlled and palladium (II) improved, 5-endo cyclization of an α-aryl-δ-epoxynitrile. The cyclization occurs with unmatched regioselectivity and high stereoselectivity. The synthesis is completed in 5 steps achieving yields of 50% for enokipodin A and 55% for enokipodin

  合成了新的全合成的伞形倍半萜烯烯配体A和B。的关键步骤涉及一种新颖的，阳离子控制和钯（II）改善，5-内切α-芳基δ-epoxynitrile的环化。环化反应具有无与伦比的区域选择性和高立体选择性。合成过程分5个步骤完成，对于enokipodin A，产率为50％，对于enokipodin B，产率为55％。
• Facile total synthesis of (±)-α-herbertenol, (±)-α-cuparenone and (±)-HM-1 methyl ether involving alkylation of hindered esters
  作者：Ashutosh Pal、Pranab Dutta Gupta、Arnab Roy、Debabrata Mukherjee

  DOI：10.1016/s0040-4039(99)00835-7

  日期：1999.6

  The total syntheses of (±)-α-herbertenol 1, (±)-α-cuparenone 4 and (±)-HM-1 methyl ether 3 have been successfully accomplished involving α,α-dimethylation of the esters 8a, 17 and 8b respectively as key steps.

  （±）-α-herbertenol的全合成1，（±）-α-cuparenone 4和（±）-HM-1甲基醚3已成功地完成涉及酯的α，α-二甲基化8A，17和图8b分别作为关键步骤。
• The First Total Synthesis of the Antimicrobial Sesquiterpenes (±)-Enokipodins A and B
  作者：A. Srikrishna、M. Srinivasa Rao

  DOI：10.1055/s-2003-45003

  日期：——

  Efficient first total synthesis of antimicrobial sesquiterpenes enokipodins A and B (1 and 2, respectively) and formal total synthesis of cuparene-1,4-diol (5) and cuparene-1,4-quinone (7) have been accomplished starting from 2,5-dimethoxy-4-methyl­acetophenone employing Claisen rearrangement and ring-closing metathesis reaction as key steps.

  以 2,5-二甲氧基-4-甲基苯乙酮为起点，以克莱森重排和闭环偏析反应为关键步骤，首次完成了抗菌倍半萜烯 enokipodins A 和 B（分别为 1 和 2）的高效全合成，并正式完成了铜蒈烯-1,4-二醇（5）和铜蒈烯-1,4-醌（7）的全合成。
• Convenient Formal Synthesis of (±)-Cuparene, (±)-Enokipodins A and B, and (±)-Cuparene-1,4-Quinone
  作者：Jean Ollivier、Pier Piras、Francesco Secci、Angelo Frongia

  DOI：10.1055/s-2007-965951

  日期：2007.4

  A Bronsted or Lewis acid mediated semi-pinacolic rearrangement effected on the diastereomers of cyclobutanol derivatives leads efficiently to useful intermediates in the synthesis of cuparene-type sesquiterpenes. The cyclobutanols are themselves easily obtainable from cyclopropyl phenyl sulfide.

  影响环丁醇衍生物的非对映异构体的布朗斯台德酸或路易斯酸介导的半频哪醇重排有效地产生了合成铜巴烯型倍半萜的有用中间体。环丁醇本身很容易从环丙基苯硫醚中获得。
• The first total synthesis of (±)-lagopodin A
  作者：A. Srikrishna、B. Vasantha Lakshmi、P.C. Ravikumar

  DOI：10.1016/j.tetlet.2005.12.071

  日期：2006.2

  The first total synthesis of (+/-)-lagopodin A and a formal total synthesis of enokipodins A and B is described. The requisite precursors containing two vicinal quaternary carbon atoms were assembled employing Claisen rearrangement and an RCM reaction as key steps starting from 2,5-dimethoxy-4-methylacetophenone. (c) 2006 Elsevier Ltd. All rights reserved.