3-(6-methoxy-2,5-dimethyl-1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionic acid methyl ester | 109251-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3-(6-methoxy-2,5-dimethyl-1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionic acid methyl ester
• 英文别名: 3-(6-Methoxy-2,5-dimethyl-1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionsaeure-methylester；Methyl 3-(6-methoxy-2,5-dimethyl-1-oxo-3,4-dihydronaphthalen-2-yl)propanoate；methyl 3-(6-methoxy-2,5-dimethyl-1-oxo-3,4-dihydronaphthalen-2-yl)propanoate
• CAS: 109251-64-1
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: KXEFJUIDVQOLRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(6-methoxy-2,5-dimethyl-1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionic acid methyl ester 在 Wilkinson's catalyst 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 氢气 、 三溴化硼 、 三溴化磷 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 叔丁醇 、 苯 为溶剂， 反应 6.0h， 生成 5,9-Dimethyl-tricyclo[7.3.1.0^1,6]tridec-5-en-4-one
  参考文献：
  名称：

  Stereocontrolled total syntheses of (±)-clovan-3-one and (±)-epi-clovan-3-one and a facile total synthesis of (±)-pseudoclovene-A

  摘要：

  Stereocontrolled total syntheses of the bridged tricyclic ketones (+/-)-clovan-3-one (5) and (+/-)-epi-clovan-3-one (6) and a facile total synthesis of the tricyclic sesquiterpene ()-pseudoclovene-A (3) have been successfully accomplished involving participation of an aryl intramolecular cyclisation of the bromophenol 11 as a key step. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01170-5
• 作为产物：
  描述：

  6-methoxy-2,5-dimethyl-α-tetralone 、 丙烯酸甲酯（MA） 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 以78%的产率得到3-(6-methoxy-2,5-dimethyl-1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionic acid methyl ester
  参考文献：
  名称：

  Stereocontrolled total syntheses of (±)-clovan-3-one and (±)-epi-clovan-3-one and a facile total synthesis of (±)-pseudoclovene-A

  摘要：

  Stereocontrolled total syntheses of the bridged tricyclic ketones (+/-)-clovan-3-one (5) and (+/-)-epi-clovan-3-one (6) and a facile total synthesis of the tricyclic sesquiterpene ()-pseudoclovene-A (3) have been successfully accomplished involving participation of an aryl intramolecular cyclisation of the bromophenol 11 as a key step. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01170-5

文献信息

• Steroids and related compounds—I
  作者：M.J. Temple Robinson

  DOI：10.1016/0040-4020(57)85010-8

  日期：1957.1

  Starting with 6-methoxy-5-methyltetralin (I), several routes to the compound (XXI) named in the title have been developed. The tetralin (I) was converted into the hexahydrophenanthrene (X) and some attempts were made to convert the latter into a 2:3-glycol or related compound with a view to changing the potential homo-D-ring into a natural D-ring before reducing the 4:12-double bond. The ketone (X)

  从6-甲氧基-5-甲基四氢萘酚（I）开始，已经开发了几种获得标题名称的化合物（XXI）的途径。将四氢化萘（I）转化为六氢菲（X），并进行了一些尝试，将后者转变为2：3-乙二醇或相关化合物，以期将潜在的均D-环转变为天然D-环在减少4：12-双键之前。通过三阶段甲基化和一，二或三阶段还原，将酮（X）转化为所需产物（XXI），改变反应的顺序以获得结构和空间特异性。当试图预测并随后合理化减少的空间过程时，发现催化剂阻碍的概念1设置在比哈德勒的构象参数的更好的引导件，其最初被施加到Δ 4 -和Δ 5个-steroids。2个
• Stereocontrolled total syntheses of (±)-clovan-3-one and (±)-epi-clovan-3-one and a facile total synthesis of (±)-pseudoclovene-A
  作者：Tapas Paul、Debabrata Mukherjee

  DOI：10.1016/s0040-4039(03)01170-5

  日期：2003.6

  Stereocontrolled total syntheses of the bridged tricyclic ketones (+/-)-clovan-3-one (5) and (+/-)-epi-clovan-3-one (6) and a facile total synthesis of the tricyclic sesquiterpene ()-pseudoclovene-A (3) have been successfully accomplished involving participation of an aryl intramolecular cyclisation of the bromophenol 11 as a key step. (C) 2003 Elsevier Science Ltd. All rights reserved.