(R)-diethyl [2′-hydroxy-(1,1′-binaphthalen)-2-yl]phosphonate | 132532-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-diethyl [2′-hydroxy-(1,1′-binaphthalen)-2-yl]phosphonate
• 英文别名: (R)-2-(diethoxyphosphoryl)-2'-hydroxy-1,1'-binaphthyl；1-(2-Diethoxyphosphorylnaphthalen-1-yl)naphthalen-2-ol
• CAS: 132532-06-0
• 化学式: C₂₄H₂₃O₄P
• 分子量: 406.418
• InChiKey: UYIBSLWWFKRCQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-diethyl [2′-hydroxy-(1,1′-binaphthalen)-2-yl]phosphonate 在 lithium aluminium tetrahydride 、 三甲基氯硅烷 、 potassium hydroxide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 (R)-2-(phosphino)-2'-methoxy-1,1'-binaphthyl
  参考文献：
  名称：

  Efficient Multigram Syntheses of Air-Stable, Chiral Primary Phosphine Ligand Precursors via Palladium-Catalyzed Phosphonylation of Aryltriflates

  摘要：

  Air-stable, chiral primary phosphines have been synthesized on a multigram scale. The key synthetic step is an optimized palladium-catalyzed phosphonylation reaction of aryltriflates, which opens up a valuable synthetic route to a chiral scaffold that is easily derivatized into novel phosphines.

  DOI：

  10.1055/s-0032-1316825
• 作为产物：
  描述：

  (R)-2-(diethoxyphosphoryl)-2'-((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 12.0h， 以89%的产率得到(R)-diethyl [2′-hydroxy-(1,1′-binaphthalen)-2-yl]phosphonate
  参考文献：
  名称：

  A New BINOL-Derived Chiral Bifunctional Phosphine Organocatalyst: Preparation and Application in Asymmetric (Aza)-Morita-Baylis-Hillman Reactions

  摘要：

  A new BINOL-derived chiral bifunctional phosphine has been designed and successfully prepared, which features a cyclic substructure of 1,3,5-diazaphosphinane. This chiral phosphine possesses good air stability in solid state, and it can be conveniently used as a relatively more nucleophilic phosphine organocatalyst. Preliminary investigations showed that it could generally afford fair to excellent yields but only modest enantioselectivity in the (aza)-Morita-Baylis-Hillman reactions of activated olefins such as ethyl acrylate and methyl vinyl ketone with aldehydes or imines. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus Sulfer and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]

  DOI：

  10.1080/10426507.2012.761987

文献信息

• A General and Facile Approach for the Synthesis of 2′-Functionalized 1,1′-Binapthyl-2-ols
  作者：Xiaomin Xie、Lina Ding、Gang Ni、Zhaoguo Zhang、Jinsheng Gao

  DOI：10.1002/cjoc.201090276

  日期：2010.9

  A facile and efficient protocol for the synthesis of 2′‐functionalized 1,1′‐binaphthyl‐2‐ols has been developed. The C,O‐dilithio reagent (2) generated by the reductive ring‐opening of binaphthofuran (1) with lithium was treated with the corresponding electrophiles to give 2′‐functionalized 1,1′‐binaphthyl‐2‐ols including the halides (3), amine (4), acid (5), aldehyde (6), carbonate (7) or phosphonate

  已经开发了一种简便有效的合成2'功能化的1,1'-联萘-2-醇的方案。将二萘并呋喃（1）与锂还原开环生成的C，O-二硫代试剂（2）用相应的亲电试剂处理，得到2'-官能化的1,1'-联萘-2-醇，包括卤化物（3），胺（4），酸（5），醛（6），碳酸盐（7）或膦酸酯（8），分别以中等至良好的产率。
• Stereospecific functionalization of (R)-(−)-1,1′-bi-2-naphthol triflate
  作者：Lilia Kurz、Gary Lee、David Morgans、Michael Joe Waldyke、Timothy Ward

  DOI：10.1016/s0040-4039(00)97053-9

  日期：1990.1
• KURZ, LILIA;LEE, GARY;MORGANS, DAVID (JR);WALDYKE, MICHAEL JOE;WARD, TIMO+, TETRAHEDRON LETT., 31,(1990) N4, C. 6321-6324
  作者：KURZ, LILIA、LEE, GARY、MORGANS, DAVID (JR)、WALDYKE, MICHAEL JOE、WARD, TIMO+

  DOI：——

  日期：——
• Efficient Multigram Syntheses of Air-Stable, Chiral Primary Phosphine Ligand Precursors via Palladium-Catalyzed Phosphonylation of Aryltriflates
  作者：Lee Higham、Arne Ficks、Connor Sibbald、Stephen Ojo、Ross Harrington、William Clegg

  DOI：10.1055/s-0032-1316825

  日期：——

  Air-stable, chiral primary phosphines have been synthesized on a multigram scale. The key synthetic step is an optimized palladium-catalyzed phosphonylation reaction of aryltriflates, which opens up a valuable synthetic route to a chiral scaffold that is easily derivatized into novel phosphines.
• A New BINOL-Derived Chiral Bifunctional Phosphine Organocatalyst: Preparation and Application in Asymmetric (Aza)-Morita-Baylis-Hillman Reactions
  作者：Chunzhang Wang、Lijun Wang、San Zeng、Silong Xu、Zhengjie He

  DOI：10.1080/10426507.2012.761987

  日期：2013.11.1

  A new BINOL-derived chiral bifunctional phosphine has been designed and successfully prepared, which features a cyclic substructure of 1,3,5-diazaphosphinane. This chiral phosphine possesses good air stability in solid state, and it can be conveniently used as a relatively more nucleophilic phosphine organocatalyst. Preliminary investigations showed that it could generally afford fair to excellent yields but only modest enantioselectivity in the (aza)-Morita-Baylis-Hillman reactions of activated olefins such as ethyl acrylate and methyl vinyl ketone with aldehydes or imines. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus Sulfer and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]