(11BS,11'BS)-4,4'-[(1R)-[1,1'-Binaphthalene]-2,2'-diylbis(oxy)]bis[dinaphtho[2,1-D:1',2'-F][1,3,2]dioxaphosphepin] | 137156-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (11BS,11'BS)-4,4'-[(1R)-[1,1'-Binaphthalene]-2,2'-diylbis(oxy)]bis[dinaphtho[2,1-D:1',2'-F][1,3,2]dioxaphosphepin]
• 英文别名: 13-[1-[2-(12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yloxy)naphthalen-1-yl]naphthalen-2-yl]oxy-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene
• CAS: 137156-21-9；149715-41-3；752210-44-9；169435-97-6；259526-87-9；954395-33-6
• 化学式: C₆₀H₃₆O₆P₂
• 分子量: 914.89
• InChiKey: UFQYDYMALACWGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.6
• 重原子数：
  68
• 可旋转键数：
  5
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (11BS,11'BS)-4,4'-[(1R)-[1,1'-Binaphthalene]-2,2'-diylbis(oxy)]bis[dinaphtho[2,1-D:1',2'-F][1,3,2]dioxaphosphepin] 在 selenium 作用下， 以 甲苯 为溶剂， 反应 17.0h， 以100%的产率得到13-Selenido-13-[1-[2-[(13-selenido-12,14-dioxa-13-phosphoniapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl)oxy]naphthalen-1-yl]naphthalen-2-yl]oxy-12,14-dioxa-13-phosphoniapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene
  参考文献：
  名称：

  Diastereoisomeric bisphosphite ligands in the hydroformylation of octenes: rhodium catalysis and HP-NMR investigations

  摘要：

  非对映异构体加氢甲酰化催化剂在催化剂预形成途径上存在差异，而 (S,S,R)-异构体的正辛烯加氢甲酰化活性则大大降低。

  DOI：

  10.1039/b814120g
• 作为产物：
  描述：

  S-1,1'-联-2-萘酚 在 4-二甲氨基吡啶 、 三乙胺 、 三氯化磷 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 (11BS,11'BS)-4,4'-[(1R)-[1,1'-Binaphthalene]-2,2'-diylbis(oxy)]bis[dinaphtho[2,1-D:1',2'-F][1,3,2]dioxaphosphepin]
  参考文献：
  名称：

  Asymmetric hydrocyanation of olefins catalyzed by chiral diphosphite–nickel complexes

  摘要：

  Chiral aryl diphosphite ligands derived from binaphthol were found to be effective in the nickel-catalyzed hydrocyanation of a variety of olefins. Enantioselective hydrocyanations of styrene, l-substituted styrenes and norbornene were achieved with excellent regioselectivity and moderate enantioselectivity. The hydrocyanation of vinyl acetate gave 72.9% ee. The catalytic activity and the enantioselectivity of the Ni(0)-diphosphite complexes were found to be highly dependent on the structures of the ligands. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00026-4

文献信息

• Enantioselective conjugate addition of diethylzinc to enones catalyzed by a copper complex of chiral aryl diphosphite
  作者：Ming Yan、Li-Wei Yang、Kwok-Yin Wong、Albert S. C. Chan

  DOI：10.1039/a807997h

  日期：——

  The 1,4-conjugate addition of diethylzinc to cyclohex-2-enone and cyclopent-2-enone catalyzed by a copper complex of a chiral aryl diphosphite gave the desired products with 90.2 and 76.6% ee respectively.

  在手性芳基二亚磷酸铜络合物的催化下，将二乙基锌与环己-2-烯酮和环戊-2-烯酮进行 1,4-共轭加成，得到了所需的产物，ee值分别为 90.2% 和 76.6%。
• Enantioselective conjugate addition of diethylzinc to cyclic enones with chiral aryl diphosphite-copper catalysts
  作者：Ming Yan、Albert S.C. Chan

  DOI：10.1016/s0040-4039(99)01272-1

  日期：1999.9

  diphosphites based on chiral binaphthol were prepared and their copper complexes were found to be efficient catalysts for the conjugate addition of diethylzinc to cyclic enones. Good enantioselectivities (up to 89.8 and 88.7% ee, respectively) were obtained in the conjugate addition of diethylzinc to 2-cyclohexenone and 2-cyclopentenone.

  制备了一系列基于手性联萘酚的C 2对称芳基亚磷酸酯，发现它们的铜配合物是将二乙基锌共轭加成环烯酮的有效催化剂。通过将二乙基锌共轭添加到2-环己烯酮和2-环戊烯酮中，可以获得良好的对映选择性（分别高达89.8和88.7％ee）。
• A convenient chromatography-free access to enantiopure 6,6′-di-tert-butyl-1,1′-binaphthalene-2,2′-diol and its 3,3′-dibromo, di-tert-butyl and phosphorus derivatives: utility in asymmetric synthesis
  作者：E. Balaraman、K.C. Kumara Swamy

  DOI：10.1016/j.tetasy.2007.06.028

  日期：2007.9

  of the hexane-soluble enantiopure 6,6′-di-tert-butyl-1,1′-binaphthalene-2,2′-diol 3 (6,6′-di-tert-butyl BINOL) using Friedel–Crafts reaction on 1,1′-binaphthalene-2,2′-diol 1 (BINOL) is described. The enantiomeric purity was fully maintained in the reaction. Compound 3 has been used as an entry point for the convenient chromatography-free synthesis of 3,3′,6,6′-tetra-tert-butyl BINOL 4 and 3,3′-dibromo-6

  一个简单的自由色谱高产合成的己烷可溶对映体纯6,6'-二-叔丁基-1,1'-联萘-2,2'-二醇3（6,6'-二-叔-描述了在1,1'-联萘-2,2'-二醇1（BINOL）上使用Friedel-Crafts反应的丁基BINOL）。反应中完全保持对映体纯度。化合物3已被用作入口点的3,3'的方便自由色谱-合成，6,6'-四-叔丁基BINOL 4和3,3'-二溴-6,6'-二-叔丁基BINOL 5。对映纯双亚磷酸酯[（6,6'-R 2 C20 H 10 O 2）P] 2 [O 2 C 20 H 10 -6,6'-R 2 ] [R = H 15，t -Bu 16 ]只需使次氯酸盐（6,6'-R 2 C 20突出显示了具有金属钠的H 10 O 2）PC1 [R = H 20，t -Bu 6 ]。15和16作为其硒氧化产物17和18的身份（在磷中心）通过X-射线晶体学证实（对映体纯形式为17，外消旋
• Chiral aryl diphosphites: a new class of ligands for hydrocyanation catalysis
  作者：Michael J. Baker、Paul G. Pringle

  DOI：10.1039/c39910001292

  日期：——

  The new diphosphite 1 derived from R-2,2′-binaphthol and its nickel(0) complex are described; optical yields for the hydrocyanation of norbornene are 38%.

  描述了衍生自R -2,2'-联萘酚的新亚磷酸酯1及其镍（0）配合物；降冰片烯氢氰化的光学产率为38％。
• Copper-catalyzed enantioselective conjugate addition of triethylaluminum to 2-cyclopentenone
  作者：Liming Su、Xingshu Li、Wing Lai Chan、Xian Jia、Albert S.C. Chan

  DOI：10.1016/s0957-4166(03)00349-5

  日期：2003.7

  Bidentate phosphites were prepared starting from BINOL, H-8-BINOL or 3,3', 5,5'-tetra-tert-butyl-2,2'-biphenol. Utilization of these ligands in the copper-catalyzed enantioselective conjugate addition of triethylaluminum to 2-cyclopentenone afforded 3-ethylcyclopentanone in up to 94.0% ee. (C) 2003 Elsevier Science Ltd. All rights reserved.