(R)-6,6'-di(2,6-xylyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-6,6'-di(2,6-xylyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate
• 英文别名: 6,20-Bis(2,6-dimethylphenyl)-13-hydroxy-12,14-dioxa-13lambda5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3(8),4,6,9,16,18(23),19,21-decaene 13-oxide；6,20-bis(2,6-dimethylphenyl)-13-hydroxy-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3(8),4,6,9,16,18(23),19,21-decaene 13-oxide
• 化学式: C₃₆H₂₉O₄P
• 分子量: 556.598
• InChiKey: PGNRSWSDZBZDIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  41
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-6,6'-di(2,6-xylyl)-1,1'-binaphthyl-2,2'-diyl chlorophosphate 在 sodium carbonate 作用下， 反应 1.0h， 以33%的产率得到(R)-6,6'-di(2,6-xylyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate
  参考文献：
  名称：

  Chiral rare earth organophosphates as homogeneous Lewis acid catalysts for the highly enantioselective hetero-Diels–Alder reactions

  摘要：

  Various trivalent rare earth-chiral phosphate complexes [(R)-l-RE, (R)-3-RE, and (R)-4-Ce] were prepared and evaluated as a Lewis acid catalyst for the asymmetric hetero-Diels-Alder reaction of aldehydes with the Danishefsky's diene. Some of them effectively promoted the reaction at room temperature in the presence or absence of achiral additives under homogeneous conditions to afford the corresponding cycloadducts with high ee's (up to 99% ee). During these reactions, remarkably high asymmetric amplifications (positive nonlinear effects) were observed as the first example in the metal ion-chiral ligand 1:3 catalytic system. A scandium catalyst bearing the H-8-BNP ligand, (R)-3-Sc, could be recovered after the reaction and successfully reused for the next round of reactions. In addition, the hetero-Diels-Alder reaction of alpha-keto esters was effectively catalyzed by the ytterbium complex, (R)-l-Yb, without any additives thus producing the asymmetric quaternary carbon in excellent enantioselectivities (up to > 99% ee). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.06.011

文献信息

• Binaphthol monophosphoric acid derivative and its use
  申请人：Tosoh Corporation

  公开号：EP1038877A1

  公开（公告）日：2000-09-27

  A binaphthol monophosphoric acid derivative of the following formula (1), (2), (3) or (4): wherein each of R1, R2, R3 and R4 which are independent of one another, is hydrogen, a C1-20 linear or branched alkyl group, a C1-20 linear or branched alkenyl group, a C1-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1-to 4-carbon atom by a C1-10 linear or branched alkynyl group, a naphthyl group or a C3-8 cycloalkyl group, provided that R1 to R4 are not simultaneously hydrogen, wherein each of R5, R6, R7 and R8 which are independent of one another, is hydrogen, a C1-20 linear or branched alkyl group, a C1-20 linear or branched alkenyl group, a C1-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1-to 4-carbon atom by a C1-10 linear or branched alkynyl group, a naphthyl group or a C3-8 cycloalkyl group.

  下式(1)、(2)、(3)或(4)的二萘酚单磷酸衍生物： 其中相互独立的 R1、R2、R3 和 R4 各为氢、C1-20 直链或支链烷基、C1-20 直链或支链烯基、C1-20 直链或支链炔基、苯基、其核在 1 至 4 碳原子上被 C1-10 直链或支链烷基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链烯基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链炔基取代的苯基、萘基或 C3-8 环烷基，条件是 R1 至 R4 不同时为氢、 其中相互独立的 R5、R6、R7 和 R8 各为氢、C1-20 直链或支链烷基、C1-20 直链或支链烯基、C1-20 直链或支链炔基、苯基、其核在 1-4 碳原子上被 C1-10 直链或支链烷基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链烯基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链炔基取代的苯基、萘基或 C3-8 环烷基。
• Highly enantioselective homogeneous catalysis of chiral rare earth phosphates in the hetero-Diels–Alder reaction
  作者：Hiroshi Furuno、Takeshi Kambara、Yumiko Tanaka、Takeshi Hanamoto、Takumi Kagawa、Junji Inanaga

  DOI：10.1016/s0040-4039(03)01460-6

  日期：2003.8

  Two types of novel rare earth (RE) complexes were synthesized and used as a chiral Lewis acid catalyst for the hetero-Diels-Alder reaction of carbonyl compounds with the Danishefsky's diene under homogeneous conditions. The Y[(R)-H-8-BNP](3) (3-Y)-catalyzed reaction of aromatic aldehydes and the Yb[(R)-BNP](3) (1-Yb)-catalyzed reaction of phenylglyoxylates afforded the corresponding cycloadducts with excellent optical purities (up to 99% ee) in high yields at room temperature. The successful recycling uses of the scandium catalyst (3-Sc) are also described. (C) 2003 Elsevier Ltd. All rights reserved.
• PROCESS FOR PREPARING (ALPHA S, BETA R)-6-BROMO-ALPHA-[2-(DIMETHYLAMINO)ETHYL]-2-METHOXY-ALPHA-1-NAPHTHALENYL-BETA-PHENYL-3-QUINOLINEETHANOL
  申请人：Janssen Pharmaceutica NV

  公开号：EP1888604B1

  公开（公告）日：2012-03-14
• Process for Preparing (Alpha S, Beta R)-6-Bromo-Alpha-[2-(Dimethylamino) Ethyl]-2-Methoxy-Alpha-1-Naphthalenyl-Beta-Phenyl-3-Quinolineethanol
  申请人：Porstmann Frank Ralf

  公开号：US20080200683A1

  公开（公告）日：2008-08-21

  The present invention relates to a process for isolating (αS,βR)-6-bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol from a mixture of stereoisomeric forms of 6-bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol by optical resolution with chiral 4-hydroxydinaphtho[2,1- d :1′,2′- f ][1,3,2]dioxaphosphepin 4-oxide or a derivative thereof, in particular (11 b R)-4-hydroxydinaphtho[2,1- d :1′,2′- f ][1,3,2]dioxaphosphepin 4-oxide, as resolution agent.
• US6274745B1
  申请人：——

  公开号：US6274745B1

  公开（公告）日：2001-08-14