(R)-3-methylene-1H-indan-1-ol | 1354785-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (R)-3-methylene-1H-indan-1-ol
• 英文别名: (R)-2,3-dihydro-3-(methylene)inden-1-ol；(R)-3-methylene-1-indanol；(R)-3-methylene-2,3-dihydro-1H-inden-1-ol；(1R)-3-methylidene-1,2-dihydroinden-1-ol
• CAS: 1354785-94-6
• 化学式: C₁₀H₁₀O
• 分子量: 146.189
• InChiKey: FWMZNYAXDOOYJE-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(2-氯苯基)-3-丁烯-1-醇 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)-3-methylene-1H-indan-1-ol 、 (S)-3-methylene-1H-indan-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

• Enantioselective Access to 3-Methylene-1H-indanol through Asymmetric Domino Allylstannylation-Heck Reaction
  作者：Hans-Günther Schmalz、Jutta Schütte、Shute Ye

  DOI：10.1055/s-0031-1289539

  日期：2011.11

  By screening various chiral P,P-ligands in the palladium-catalyzed reaction of ortho-iodobenzaldehyde with allyl tributylstannane, a suitable ligand (Taniaphos) was identified that affords 3-methylene-1-indanol with an enantioselectivity of 96% ee. This result indicates that a ligated palladium intermediate is involved in the chirogenic step of the catalytic cycle (intramolecular electrophilic activation

  通过在钯催化的邻碘联苯甲醛与烯丙基三丁基锡烷的反应中筛选各种手性P，P-配体，确定了合适的配体（Taniaphos），该对映体提供了3-亚甲基-1-茚满醇，对映选择性为96％ee。该结果表明，连接的钯中间体参与催化循环的生色步骤（通过邻位钯催化醛官能团的分子内亲电活化）。 钯-对映选择性催化-烯丙基-锡烷-分子内-Heck反应-多米诺反应-手性P，P-配体
• 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.
• A catalytic asymmetric approach to C1-chiral 3-methylene-indan-1-ols
  作者：Roya Mirabdolbaghi、Travis Dudding

  DOI：10.1016/j.tet.2011.12.040

  日期：2012.2

  (Ph3P)2PdIICl2 (bis(triphenylphosphine)palladium(II) dichloride) (2 mol %) catalyzed asymmetric Sakurai–Hosomi–Yamamoto allylation/Mizoroki–Heck reaction that affords C1-chiral 3-methylene-indan-1-ols with enantiomeric excess (ee) up to 80% is reported. Notably, this protocol allows for the use of various o-substituted benzaldehydes and allyltrimethoxysilane. It was also discovered that the presence of electron-rich

  （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。