13-tert-butyl-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 | 344611-55-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 13-tert-butyl-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: 344611-55-8
• 化学式: C₂₄H₂₁O₂P
• 分子量: 372.403
• InChiKey: UEPRZUTTXIDGES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  13-tert-butyl-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 以62%的产率得到
  参考文献：
  名称：

  OVCHINNIKOV, V. V.;CHERKASOVA, O. A.;VERIZHNIKOV, L. V., ZH. OBSHCH. XIMII, 1982, 52, N 3, 707-708

  摘要：

  DOI：
• 作为产物：
  描述：

  S-1,1'-联-2-萘酚 、 叔丁基二氯化膦 在 三乙胺 作用下， 以 乙醚 为溶剂， 以95%的产率得到13-tert-butyl-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
  参考文献：
  名称：

  Phenol-Derived Chiral Auxiliaries as Substrates in the Synthesis of Optically Active Phosphonic Acid Derivatives: Synthetic and Structural Aspects

  摘要：

  Preparation of chiral phosphonic acid amidoesters or diesters derived from diastereomerically pure 1-[alpha-N-1-phenylethylamino]benzyl-2-naphthol or 2,2 '-dihydroxy-1,1 '-binaphthyl are reported. The attempted ring opening reactions of the isolated compounds with a few nucleophiles are also discussed. Basic structural data for phenyl amidophosphonate and phenylamidothiophosphonate derived from diastereomerically pure 1-[alpha-N-1-phenylethylamino]benzyl-2-naphthol based on X-ray structural analysis are also presented.

  DOI：

  10.1080/10426507.2014.974096
• 作为试剂：
  描述：

  1-(乙酰氨基)-1-苯乙烯 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 13-tert-butyl-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 、 [(S)-1,1'-binaphthalen-2,2'-diyloxy](methyl)phosphine 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、130.0 kPa 条件下， 生成 (R)-(+)-N-乙酰基-甲基苄胺 、 (S)-(-)-N-乙酰基-1-甲基苄胺
  参考文献：
  名称：

  使用手性单齿P配体的混合物在Rh催化的不对称烯烃加氢中的非线性效应。

  摘要：

  DOI：

  10.1002/anie.200503604

文献信息

• Chloro- and phenoxy-phosphines in frustrated Lewis pair additions to alkynes
  作者：Christopher B. Caputo、Stephen J. Geier、Eva Y. Ouyang、Christoph Kreitner、Douglas W. Stephan

  DOI：10.1039/c1dt11196e

  日期：——

  The reaction of tBu(C6H4O2)P, with the borane B(C6F5)3 gives rise to NMR data consistent with the formation of the classical Lewis acid–base adduct tBu(C6H4O2)P(B(C6F5)3) (1). In contrast, the NMR data for the corresponding reactions of tBu(C20H12O2)P and Cl(C20H12O2)P with B(C6F5)3 were consistent with the presence of equilibria between free phosphine and borane and the corresponding adducts. Nonetheless, in each case, the adducts tBu(C20H12O2)P(B(C6F5)3) (2) and Cl(C20H12O2)P(B(C6F5)3) (3) were isolable. The species 1 reacts with PhCCH to give the new species tBu(C6H4O2)P(Ph)CCHB(C6F5)3 (4) in near quantitative yield. In an analogous fashion, the addition of PhCCH to solutions of the phosphinestBu(C20H12O2)P, tBuPCl2 and (C6H3(2,4-tBu2)O)3P each with an equivalent of B(C6F5)3 gave rise to L(Ph)CCHB(C6F5)3 (L = tBu(C20H12O2)P5, tBuPCl26 and (C6H3(2,4-tBu2)O)3P 7). X-Ray data for 1, 2, 6 and 7 are presented. The implications of these findings are considered.

  tBu(C6H4O2)P 与硼烷 B(C6F5)3 反应产生的核磁共振数据与经典的路易斯酸碱加合物 tBu(C6H4O2)P(B(C6F5)3) 的形成一致 (1)。相反，tBu(C20H12O2)P 和 Cl(C20H12O2)P 与 B(C6F5)3 的相应反应的核磁共振数据则与游离膦和硼烷与相应加合物之间存在平衡一致。不过，在每种情况下，加合物 tBu(C20H12O2)P(B(C6F5)3) (2) 和 Cl(C20H12O2)P(B(C6F5)3) (3) 都是可以分离的。物种 1 与 PhCCH 反应生成新物种 tBu(C6H4O2)P(Ph)CCHB(C6F5)3(4)，产量接近定量。以类似的方式，将 PhCCH 加入到膦化物 Bu(C20H12O2)P、tBuPCl2 和 (C6H3(2,4-tBu2)O)3P 的溶液中，每种膦化物都含有等量的 B(C6F5)3，从而得到 L(Ph)CCHB(C6F5)3 （L = tBu(C20H12O2)P5、tBuPCl26 和 (C6H3(2,4-tBu2)O)3P 7）。文中给出了 1、2、6 和 7 的 X 射线数据。研究还探讨了这些发现的意义。
• 3,3,3',3'-TETRAMETHYL-1,1'-SPIROBIINDANE-7,7'-DIOL
  申请人：ZHEJIANG UNIVERSITY

  公开号：US20220213015A1

  公开（公告）日：2022-07-07

  Provided herein is 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol, which is a compound represented by formula I, or an enantiomer or a raceme thereof. The 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol is prepared with a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-dicarbaldehyde derivative as a starting material through a Baeyer-Villiger oxidation rearrangement reaction and an alkaline hydrolysis reaction. The 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol comprises two gem-dimethyl groups and is a key intermediate for preparing corresponding 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based monophosphine ligands, such as phosphonite ligands, phosphite ligands, phosphoramidite ester ligands, phosphoric acid and phsophonamidate. The 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol skeleton provided herein could be used in chemical industry and has economic practicality and industrial application prospects.
• US7704912B2
  申请人：——

  公开号：US7704912B2

  公开（公告）日：2010-04-27
• Nonlinear Effects in Rh-Catalyzed Asymmetric Olefin Hydrogenation Using Mixtures of Chiral Monodentate P Ligands
  作者：Manfred T. Reetz、Yu Fu、Andreas Meiswinkel

  DOI：10.1002/anie.200503604

  日期：2006.2.20
• Phenol-Derived Chiral Auxiliaries as Substrates in the Synthesis of Optically Active Phosphonic Acid Derivatives: Synthetic and Structural Aspects
  作者：Józef Drabowicz、Dorota Krasowska、Andrzej Łopusiński、Anna Aftyka、Patrycja Pokora-Sobczak、Małgorzata Urbaniak、Małgorzata Szyrej、Wanda Wieczorek

  DOI：10.1080/10426507.2014.974096

  日期：2015.6.3

  Preparation of chiral phosphonic acid amidoesters or diesters derived from diastereomerically pure 1-[alpha-N-1-phenylethylamino]benzyl-2-naphthol or 2,2 '-dihydroxy-1,1 '-binaphthyl are reported. The attempted ring opening reactions of the isolated compounds with a few nucleophiles are also discussed. Basic structural data for phenyl amidophosphonate and phenylamidothiophosphonate derived from diastereomerically pure 1-[alpha-N-1-phenylethylamino]benzyl-2-naphthol based on X-ray structural analysis are also presented.