(R)-6-methoxy-3-methylene-2,3-dihydro-1H-inden-1-ol | 1360053-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (R)-6-methoxy-3-methylene-2,3-dihydro-1H-inden-1-ol
• 英文别名: (1R)-2,3-dihydro-6-methoxy-3-(methylene)inden-1-ol；(R)-6-methoxy-3-methylene-1H-indan-1-ol；(1R)-6-methoxy-3-methylidene-1,2-dihydroinden-1-ol
• CAS: 1360053-05-9
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: SOWKPQFFJUPUMA-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2-bromo-5-methoxyphenyl)but-3-en-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (R)-6-methoxy-3-methylene-2,3-dihydro-1H-inden-1-ol 、 (S)-6-methoxy-3-methylene-2,3-dihydro-1H-inden-1-ol
  参考文献：
  名称：

  C 1-手性3-亚甲基-茚满-1-醇的催化不对称方法

  摘要：

  （R）-BINAP·Ag I F（2,2'-双（二苯基膦基）-1,1'-联萘基）（6-10 mol％）和（Ph 3 P）2 Pd II Cl 2（bis （三苯基膦）二氯化钯（II）（2 mol％）催化不对称Sakurai–Hosomi–Yamamoto烯丙基化/ Mizoroki–Heck反应，得到C 1-手性3-亚甲基-茚满-1-醇，对映体过量（ee）高达据报道80％。值得注意的是，此协议允许使用各种的ö-取代的苯甲醛和烯丙基三甲氧基硅烷。还发现富电子基团的存在对反应的对映选择性没有影响，而吸电子基团导致产物ee的腐蚀。

  DOI：

  10.1016/j.tet.2011.12.040

文献信息

• Palladium/ClickFerrophos-Catalyzed Asymmetric Domino Allylstannylation–Heck Reaction of <i>o</i>-Formylaryl Triflate
  作者：Atsuo Tada、Yuichiro Tokoro、Shin-ichi Fukuzawa

  DOI：10.1021/jo5010247

  日期：2014.9.5

  Asymmetric domino allylstannylation-Heck reaction of o-formylaryl triflates was successively catalyzed by Pd/ClickFerrophos to give the 3-methylene-indan-1-ols in good yields with good to excellent enantioselectivities. The benefit of the reaction is that the starting o-formylaryl triflates are prepared from easily accessible salicylaldehyde derivatives, and the variation of the product, chiral 3-methylene-indan-1-ols, can be expanded. The reaction with 4-substituted substrates gave the corresponding 3-methylene-indan-1-ols in good yields with high enantioselectivities, whereas the reaction with 5- and 6-substituted substrates occasionally afforded the corresponding Stille coupling product in significant amounts along with the desired 3-methylene-indan-1-ols.
• Enantioselective Synthesis of 3-Methyleneindan-1-ols via a One-Pot Allylboration–Heck Reaction of 2-Bromobenzaldehydes
  作者：Ewen D. D. Calder、Andrew Sutherland

  DOI：10.1021/acs.orglett.5b01047

  日期：2015.5.15

  A novel, one-pot allylboration-Heck reaction of 2-bromobenzaldehydes has been developed for the general and efficient synthesis of 3-methyleneindan-1-ols. Modification of the one-pot procedure to include chiral Bronsted acid catalyzed allylation has allowed the preparation of these building blocks in high enantioselectivity and excellent yields.