(R)-1-(3,4-methylenedioxyphenyl)-1-propanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (R)-1-(3,4-methylenedioxyphenyl)-1-propanol
• 英文别名: (+)-(R)-marginatumol；(R)-1-(benzo[d][1,3]dioxol-5-yl)propan-1-ol；(1R)-1-(1,3-benzodioxol-5-yl)propan-1-ol
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: PXFYAFDHWSXVLU-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+)-(R)-1-(3,4-methylenedioxyphenyl)propyl acetate 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以77%的产率得到(R)-1-(3,4-methylenedioxyphenyl)-1-propanol
  参考文献：
  名称：

  Chemical constituents from Piper marginatum Jacq. (Piperaceae)—antifungal activities and kinetic resolution of (RS)-marginatumol by Candida antarctica lipase (Novozym 435)

  摘要：

  The leaves of Piper marginatum contain the antifungal compounds 3,4-methylenedioxypropiophenone 1, 2-methoxy-4,5-methylenedioxypropiophenone 2, 1-(3,4-methylenedioxyphenyl)propan-1-ol 3 (marginatumol), 5,4'-dihydroxy-7-methoxyflavanone 4 and 5,7-dihydroxy-4'-methoxyflavanone 5. The absolute configuration of natural marginatumol was deter-mined as (+)-(R)-3 (ee 48%) by comparison of its optical properties with the chiral forms obtained by kinetic resolution of racemic 3 using Candida antarctica lipase (Novozym 435). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.006

文献信息

• Enantioselective Addition of Organozinc Reagents to Aldehydes Catalyzed by 3,3′-Bis(diphenylphosphinoyl)-BINOL
  作者：Manabu Hatano、Takashi Miyamoto、Kazuaki Ishihara

  DOI：10.1002/adsc.200505221

  日期：2005.10

  The enantioselective addition of organozinc reagents to aromatic and aliphatic aldehydes 1 gives secondary alcohols 2 with excellent enantioselectivities in high yields through the catalytic use of (R)-3,3′-bis(diphenylphosphinoyl)-BINOL (3) or (R)-3,3′-bis(diphenylthiophosphinoyl)-BINOL (4) without Ti(IV) complexes. The coordination of the O or S atom of a (thio)phosphinoyl group bearing a BINOL backbone

  通过对（R）-3,3'-双（二苯基膦酰基）-BINOL（3）或（R）-的催化使用，将有机锌试剂对映选择性地添加到芳族和脂族醛1中，从而以高收率获得具有优异对映选择性的仲醇2。没有Ti（IV）配合物的3，3′-双（二苯基硫代膦酰基）-BINOL（4）。带有BINOL骨架的（硫代）膦酰基的O或S原子与有机锌试剂的配位可以有效地提高有机锌试剂的亲核性。
• 3,3‘-Diphosphoryl-1,1‘-bi-2-naphthol−Zn(II) Complexes as Conjugate Acid−Base Catalysts for Enantioselective Dialkylzinc Addition to Aldehydes
  作者：Manabu Hatano、Takashi Miyamoto、Kazuaki Ishihara

  DOI：10.1021/jo060908t

  日期：2006.8.1

  A highly enantioselective dialkylzinc (R22Zn) addition to a series of aromatic, aliphatic, and heteroaromatic aldehydes (5) was developed based on conjugate Lewis acid−Lewis base catalysis. Bifunctional BINOL ligands bearing phosphine oxides [P(O)R2] (7), phosphonates [P(O)(OR)2] (8 and 9), or phosphoramides [P(O)(NR2)2] (10) at the 3,3‘-positions were prepared by using a phospho-Fries rearrangement

  基于共轭路易斯酸-路易斯碱催化，开发了对一系列芳族，脂族和杂芳族醛（5）的高对映选择性二烷基锌（R 2 2 Zn）。带有氧化膦[P（O）R 2 ]（7），膦酸酯[P（O）（OR）2 ]（8和9）或磷酰胺[P（O）（NR 2）2 ]（10的双功能BINOL配体）通过使用磷酸化-弗里斯重排作为关键步骤来制备3,3'-位。NaphO-Zn（II）-R 2的配位中心以路易斯酸为底物上的羰基，并在3,3'-二磷酰基-BINOL-Zn（II）中以磷酰基（PO）为路易斯碱活化R 2 2 Zn（II）催化剂可以以高对映选择性（高达> 99％ee）促进碳-碳键的形成。通过X射线分析游离配体（7）和四核Zn（II）团簇（21）进行了机理研究，对Zn（II）配合物进行31 P NMR实验，在配体之间没有非线性效应（7））和苯甲醛的Et加合物，以及与某些手性或非手性Zn（II）配合物的化学计量反应，提出了一种包含单体活性中间体的过渡态组装体。
• Enantioselective Dialkylzinc Addition to Aldehydes Catalyzed by Chiral Zn(II)-BINOLates Bearing Phosphonates and Phosphoramides in the 3,3′-Positions
  作者：Kazuaki Ishihara、Manabu Hatano、Takashi Miyamoto

  DOI：10.1055/s-2006-944201

  日期：2006.7

  Highly enantioselective dialkylzinc addition to a series of aldehydes was developed based on chiral Zn(II)-BINOLate catalysts bearing phosphonates [P(=O)(OR) 2 ] and phosphoramides [P(=O)(NMe 2 ) 2 ] at the 3,3'-positions. The reactions proceeded smoothly and showed reductions in the amounts of both catalysts and dialkylzinc reagents to be loaded.

  基于带有膦酸酯 [P(=O)(OR) 2 ] 和磷酰胺 [P(=O)(NMe 2 ) 2 ] 的手性 Zn(II)-BINOLate 催化剂，开发了对一系列醛的高对映选择性二烷基锌加成3,3'-位置。反应进行得很顺利，催化剂和二烷基锌试剂的负载量都有所减少。
• Highly Enantioselective Addition of Dialkylzincs to Aromatic Aldehydes Using 1-Phenyl-2-(1-pyrrolidinyl)-1-propanol as a Chiral Catalyst
  作者：Kenso Soai、Takashi Konishi、Takanori Shibata

  DOI：10.3987/com-99-8532

  日期：——

  (1S,2R)- and (1R,2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol catalyzes the enantioselective addition of dialkylzincs to aromatic aldehydes to afford enantiomerically enriched aromatic sec-alcohols with up to 92% enantiomeric excess.

  (1S,2R)-和(1R,2S)-1-苯基-2-(1-吡咯烷基)-1-丙醇能够催化二烷基锌与芳香醛之间的对映选择性加成反应，生成具有高达92%对映体过量的芳族仲醇。
• Novel<i>C</i> ₂-Symmetric 1,1′-Disubstituted Ferrocenyl Aziridino Alcohol Ligands: Remarkable Improvement of Enantioselectivity in the Catalytic Asymmetric Addition of Diethylzinc to Aldehydes
  作者：Min-Can Wang、Xue-Hui Hou、Cui-Lian Xu、Lan-Tao Liu、Gui-Lan Li、De-Kun Wang

  DOI：10.1055/s-2005-916038

  日期：——

  A series of novel chiral C 2 -symmetric 1,1'-disubstituted ferrocenyl aziridino alcohols have been readily synthesized and applied as catalysts to promote enantioselective addition of diethylzinc to aldehydes affording thecorresponding 1-propanols in up to 99.5% enantiomeric excess with excellent yields. The effect of the ligand structure on the enantioselectivity was examined. The results showed that

  一系列新型手性 C 2 -对称 1,1'-二取代二茂铁氮丙啶醇已被容易地合成并用作催化剂，以促进二乙基锌与醛的对映选择性加成，从而以高达 99.5% 的对映体过量提供相应的 1-丙醇，并具有优异的收率。研究了配体结构对对映选择性的影响。结果表明，C 2 -对称二茂铁基β-氨基醇配体可以为二乙基锌与醛的不对称加成产生良好的不对称环境。X射线衍射分析证实了手性C 2 -对称二茂铁氮丙啶醇配体8j的绝对构型。