(11S,12R)-9,10-乙桥-9,10-二氢蒽-11,12-二甲酸 | 23194-05-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 中文名称: (11S,12R)-9,10-乙桥-9,10-二氢蒽-11,12-二甲酸
• 英文名称: 9,10-dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylic acid
• 英文别名: tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-dicarboxylic acid
• CAS: 23194-05-0
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: NYMGGONMSRTFKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (11S,12R)-9,10-乙桥-9,10-二氢蒽-11,12-二甲酸 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到11,12-Bis-hydroxymethyl-9,10-dihydro-9,10-ethano-anthracen
  参考文献：
  名称：

  Palladium Complexes with Bulky Diphosphine Ligands as Highly Selective Catalysts for the Synthesis of (Bio-) Adipic Acid from Pentenoic Acid Mixtures.

  摘要：

  A series of sterically bulky diphosphines have been prepared, including P-2 = trans-1,2-bis[(di-tert-butylphosphino)methyllcydohexane (4), (2-methylenepropane1,3-diy1)bis(di-tert-butylphosphine) (5), bis[(di-tertbutylphosphino)methyl]dimethylsilane (6), and cis- and trans11,12-bis [ (di-tert-butylphosphino)methy1]-9,10-dihydro-9,10-ethanoanthracene (10 and 11). The corresponding palladium complexes of these ligands, P2Pd(CF3CO2)(2), have been synthesized and characterized. The solid-state structures of [Pd(4)(CF3CO2)(2)], [Pd(S)(CF3CO2)(2)], [Pd(6)(CF3CO2)(2)], and [Pd(11)(CF3CO2)(2)] were obtained by single-crystal X-ray diffraction and confirm the bidentate binding mode of the ligand and a square-planar coordination geometry with a minor distortion from the ideal. The diphosphines in combination -with Pd(OAc)(2) have been applied in the hydroxycarbonylation of a mixture of pentenoic acid isomers to produce adipic acid with high selectivity (in several cases >95%). The (regio)selectivity of the hydroxycarbonylation reaction is highly dependent on the P-2 diphosphine ligand structure, particularly the steric bulk of the substituents on the diphosphine donor and the P-Pd-P bite angle in the complexes, with respectively tertiary alkyl phosphine substituents (tert-butyl, adamantyl) and a C4 backbone P-Pd-P bite angle >100 degrees being the common features of highly adipic acid selective systems. It is suggested that the regioselectivity of hydroxycarbonylation becomes largely driven by the chelation of the carboxylic acid functionality of pentenoic acid substrates, when smaller size P substituents and/or when P-2 ligands with smaller bite angles (<100 degrees) are applied.

  DOI：

  10.1021/acs.organomet.5b00517
• 作为产物：
  描述：

  9,10-二氢蒽 、 富马酸 以 1,4-二氧六环 为溶剂， 生成 (11S,12R)-9,10-乙桥-9,10-二氢蒽-11,12-二甲酸
  参考文献：
  名称：

  Palladium Complexes with Bulky Diphosphine Ligands as Highly Selective Catalysts for the Synthesis of (Bio-) Adipic Acid from Pentenoic Acid Mixtures.

  摘要：

  A series of sterically bulky diphosphines have been prepared, including P-2 = trans-1,2-bis[(di-tert-butylphosphino)methyllcydohexane (4), (2-methylenepropane1,3-diy1)bis(di-tert-butylphosphine) (5), bis[(di-tertbutylphosphino)methyl]dimethylsilane (6), and cis- and trans11,12-bis [ (di-tert-butylphosphino)methy1]-9,10-dihydro-9,10-ethanoanthracene (10 and 11). The corresponding palladium complexes of these ligands, P2Pd(CF3CO2)(2), have been synthesized and characterized. The solid-state structures of [Pd(4)(CF3CO2)(2)], [Pd(S)(CF3CO2)(2)], [Pd(6)(CF3CO2)(2)], and [Pd(11)(CF3CO2)(2)] were obtained by single-crystal X-ray diffraction and confirm the bidentate binding mode of the ligand and a square-planar coordination geometry with a minor distortion from the ideal. The diphosphines in combination -with Pd(OAc)(2) have been applied in the hydroxycarbonylation of a mixture of pentenoic acid isomers to produce adipic acid with high selectivity (in several cases >95%). The (regio)selectivity of the hydroxycarbonylation reaction is highly dependent on the P-2 diphosphine ligand structure, particularly the steric bulk of the substituents on the diphosphine donor and the P-Pd-P bite angle in the complexes, with respectively tertiary alkyl phosphine substituents (tert-butyl, adamantyl) and a C4 backbone P-Pd-P bite angle >100 degrees being the common features of highly adipic acid selective systems. It is suggested that the regioselectivity of hydroxycarbonylation becomes largely driven by the chelation of the carboxylic acid functionality of pentenoic acid substrates, when smaller size P substituents and/or when P-2 ligands with smaller bite angles (<100 degrees) are applied.

  DOI：

  10.1021/acs.organomet.5b00517

文献信息

• <i>trans</i>-9,10-Dihydro-9,10-ethanoanthracene-11,12-dicarboxylic Acid: Remarkable Host Selectivities in the Presence of Mixtures of Anisole and Bromoanisole Isomers
  作者：Benita Barton、Mino R. Caira、Ulrich Senekal、Eric C. Hosten

  DOI：10.1021/acs.cgd.2c01147

  日期：2023.1.4

  Furthermore, this striking host selectivity persisted even in binary solutions containing low concentrations of 4-BA (18–25%); near-complete selectivities in favor of 4-BA were observed here too. Single crystal X-ray diffraction analyses showed that the favored guest species, 4-BA, was the only one to experience short intermolecular contacts, through its phenyl ring, with the host molecule’s carbonyl oxygen

  在这项工作中，反式-9,10-二氢-9,10-乙基蒽-11,12-二羧酸 ( DED)，一种与苯甲醚 (ANI)、2-溴苯甲醚 (2-BA) 和 4-溴苯甲醚 (4-BA) 形成复合物的主体化合物被发现对 4-BA 具有显着的亲和力 (93.1–98.6%)当从含有该客体的任何混合物中重结晶时，这些二元（ANI/4-BA、2-BA/4-BA 或 3-BA/4-BA）、三元（ANI/2-BA/4-BA、 ANI/3-BA/4-BA, or 2-BA/3-BA/4-BA), or quaternary (ANI/2-BA/3-BA/4-BA) in nature. 此外，这种显着的宿主选择性甚至在含有低浓度 4-BA (18–25%) 的二元溶液中仍然存在；此处也观察到接近完全的有利于 4-BA 的选择性。单晶 X 射线衍射分析表明，受欢迎的客体物种 4-BA 是唯一通过其苯环经历短分子间接触
• Resist composition, and method of forming resist pattern
  申请人：TOKYO OHKA KOGYO CO., LTD.

  公开号：US11256169B2

  公开（公告）日：2022-02-22

  A resist composition containing a resin component having a structural unit containing a group which is dissociated under the action of an acid and compound represented by the general formula (bd1). In the formula (bd1), Rx1 to Rx4 represent a hydrocarbon group or a hydrogen atom or may be mutually bonded to form a ring structure, Ry1 to Ry2 represent a hydrocarbon group or a hydrogen atom or may be mutually bonded to form a ring structure, and Rz1 to Rz4 represent a hydrocarbon group or a hydrogen atom or may be mutually bonded to form a ring structure. At least one of Rx1 to Rx4, Ry1 to Ry2 and Rz1 to Rz4 has an anion group, the entire anion moiety may be an n-valent anion, and Mm+ represents an m-valent organic cation

  一种抗蚀剂组合物，含有一种树脂成分，其结构单元含有一个在酸作用下可离解的基团和通式（bd1）所代表的化合物。在通式（bd1）中，Rx1 至 Rx4 代表烃基或氢原子，或可相互键合形成环状结构；Ry1 至 Ry2 代表烃基或氢原子，或可相互键合形成环状结构；Rz1 至 Rz4 代表烃基或氢原子，或可相互键合形成环状结构。Rx1至Rx4、Ry1至Ry2和Rz1至Rz4中至少有一个具有阴离子基团，整个阴离子分子可以是n价阴离子，Mm+代表m价有机阳离子。
• Resist composition, method of forming resist pattern, compound, and acid generator
  申请人：TOKYO OHKA KOGYO CO., LTD.

  公开号：US11221557B2

  公开（公告）日：2022-01-11

  A resist composition containing a compound represented by the general formula (bd1-1), (bd1-2) or (bd1-3); in the formula, Rx1 to Rx4 represent a hydrocarbon group or a hydrogen atom or may be mutually bonded to form a ring structure; Ry1 to Ry2 represent a hydrocarbon group or a hydrogen atom or may be mutually bonded to form a ring structure, Rz1 to Rz4 represent a hydrocarbon group or a hydrogen atom or may be mutually bonded to form a ring structure. At least one of Rx1 to Rx4, Ry1 to Ry2 and Rz1 to Rz4 has an anion group, M1m+ represents a sulfonium cation having a sulfonyl group, R001 to R003 each independently represent a monovalent organic group; provided that at least one of R001 to R003 is an organic group having an acid dissociable group; and M3m+ represents an m-valent organic cation having an electron-withdrawing group.

  一种含有通式(bd1-1)、(bd1-2)或(bd1-3)所代表的化合物的抗蚀剂组合物；在通式中，Rx1至Rx4代表烃基或氢原子，或可相互键合形成环状结构；Ry1至Ry2代表烃基或氢原子，或可相互键合形成环状结构，Rz1至Rz4代表烃基或氢原子，或可相互键合形成环状结构。Rx1至Rx4、Ry1至Ry2和Rz1至Rz4中至少有一个具有阴离子基团，M1m+代表具有磺酰基的锍阳离子，R001至R003各自独立地代表一价有机基团；条件是R001至R003中至少有一个是具有酸可解离基团的有机基团；M3m+代表具有抽电子基团的m价有机阳离子。
• DOEBLER, CHR.;KREUZFELD, H. -J., J. PRAKT. CHEM., 1983, 325, N 6, 1021-1026
  作者：DOEBLER, CHR.、KREUZFELD, H. -J.

  DOI：——

  日期：——
• SALTS OF PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1091958A1

  公开（公告）日：2001-04-18