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1,8-dichloro-9,10-ethano-9,10-dihydroanthracene | 38366-40-4

中文名称
——
中文别名
——
英文名称
1,8-dichloro-9,10-ethano-9,10-dihydroanthracene
英文别名
1,8-dichloro-9,10-dihydro-9,10-ethanoanthracene;1,8-Dichlor-9,10-ethanoanthracen;3,13-Dichlorotetracyclo[6.6.2.02,7.09,14]hexadeca-2(7),3,5,9(14),10,12-hexaene
1,8-dichloro-9,10-ethano-9,10-dihydroanthracene化学式
CAS
38366-40-4
化学式
C16H12Cl2
mdl
——
分子量
275.177
InChiKey
LCPFKYONGPNRPS-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    5.5
  • 重原子数:
    18
  • 可旋转键数:
    0
  • 环数:
    5.0
  • sp3杂化的碳原子比例:
    0.25
  • 拓扑面积:
    0
  • 氢给体数:
    0
  • 氢受体数:
    0

反应信息

  • 作为反应物:
    描述:
    1,8-dichloro-9,10-ethano-9,10-dihydroanthracene二苯基氯化膦sodiumlithium 作用下, 以 四氢呋喃 为溶剂, 反应 6.0h, 以69%的产率得到1,8-bis(diphenylphosphino)-9,10-ethano-9,10-dihydroanthracene
    参考文献:
    名称:
    Highly Efficient Nickel-Catalyzed 2-Methyl-3-butenenitrile Isomerization: Applications and Mechanistic Studies Employing the TTP Ligand Family
    摘要:
    A series of sterically and electronically fine-tuned, chelating diphosphine ligands were synthesized. The ligands are analogues of Triptyphos (TTP, 1), all based upon a variably 9,10-two-carbon-bridged 9,10-dihydroanthracene scaffold. These new TTP-type ligands were employed in the Ni(0)-catalyzed isomerization of 2-methyl-3-butenenitrile (2M3BN), one of the key steps of industrial adiponitrile production by the DuPont process. The reaction showed a surprising preference for ligands bearing electron-donating substituents, such as methoxy or methyl groups, in the phenyl para position of the Ni-ligating PPh2 units. Octyltriptyphos (3) afforded the highest 2M3BN-isomerization turnover rate yet reported. A series of deuterium-labeling experiments was performed to investigate the possibility of an isomerization mechanism consisting of a cascade of de- and rehydrocyanation steps, which could be excluded. Using the ethano-bridged ligand 4, complex 16a (4-kappa P:kappa P')Ni(eta(3)-C4H7)CN (supposedly an intermediate of the 2M3BN-isomerization reaction) was isolated, and its solid-state structure was determined by X-ray diffraction analysis. The complete catalytic cycle of 2M3BN isomerization with ligand 4, as suggested by the available experimental evidence, was modeled using DFT methods.
    DOI:
    10.1021/om200164f
  • 作为产物:
    参考文献:
    名称:
    Dissociation constants of 8-substituted 9,10-ethanoanthracene-1-carboxylic acids and related compounds. Evidence for the field model for the polar effect
    摘要:
    DOI:
    10.1021/ja00764a032
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文献信息

  • Phospor, arsenic and antimony compounds based upon diaryl-anellated diaryl-anellated bicyclo'2.2.n! parent substances and catalysts containing same
    申请人:——
    公开号:US20030055253A1
    公开(公告)日:2003-03-20
    Novel compounds of phosphorus, of arsenic and of antimony can be used as ligands to form complexes of metals of transition group VIII which can be used in catalysts for hydroformylation, hydrocyanation, carbonylation, hydrogenations, oligomerization and polymerization of olefins and for metathesis.
    磷、砷和锑的新化合物可以用作配体,形成过渡金属VIII族金属的配合物,可以用于羰基化、氢化、寡聚和聚合烯烃以及交换反应的催化剂中。
  • VERBINDUNGEN DES PHOSPHORS, ARSENS UND DES ANTIMONS BASIEREND AUF DIARYLANELLIERTEN BICYCLO[2.2.N]-GRUNDKÖRPERN UND DIESE ENTHALTENDE KATALYSATOREN
    申请人:BASF AKTIENGESELLSCHAFT
    公开号:EP1257361B1
    公开(公告)日:2003-11-26
  • US6977312B2
    申请人:——
    公开号:US6977312B2
    公开(公告)日:2005-12-20
  • [DE] VERBINDUNGEN DES PHOSPHORS, ARSENS UND DES ANTIMONS BASIEREND AUF DIARYLANELLIERTEN BICYCLO`2.2.N!-GRUNDKÖRPERN UND DIESE ENTHALTENDE KATAKYSATOREN<br/>[EN] PHOSPHOR, ARSENIC AND ANTIMONY COMPOUNDS BASED UPON DIARYL-ANELLATED BICYCLO`2.2.N! PARENT SUBSTANCES AND CATALYSTS CONTAINING SAME<br/>[FR] COMPOSES DU PHOSPHORE, DE L'ARSENIC ET DE L'ANTIMOINE A BASE DE CORPS DE BASE BICYCLO `2.2.N! DIARYLANNELES
    申请人:BASF AG
    公开号:WO2001058589A1
    公开(公告)日:2001-08-16
    Die vorliegende Erfindung betrifft Verbindungen des Phosphors, Arsens und des Antimons, basierend auf diarylanellierten Bicyclo `2.2.n!-Grundkörpen, ein Verfahren zu ihrer Herstellung und einen Katalysator, der wenigstens einen Komplex eines Metalls der VIII. Nebengruppe mit einer solchen Verbindung als Liganden umfasst. Die Erfindung betrifft weiterhin die Verwendung dieser Katalysatoren zur Hydroformylierung, Hydrocyanierung, Carbonylierung, Hydrierung, Olefinoligomerisierung und -polymerisierung sowie zur Metathese.
  • Highly Efficient Nickel-Catalyzed 2-Methyl-3-butenenitrile Isomerization: Applications and Mechanistic Studies Employing the TTP Ligand Family
    作者:Michael E. Tauchert、Daniel C. M. Warth、Sebastian M. Braun、Irene Gruber、Alexandra Ziesak、Frank Rominger、Peter Hofmann
    DOI:10.1021/om200164f
    日期:2011.5.23
    A series of sterically and electronically fine-tuned, chelating diphosphine ligands were synthesized. The ligands are analogues of Triptyphos (TTP, 1), all based upon a variably 9,10-two-carbon-bridged 9,10-dihydroanthracene scaffold. These new TTP-type ligands were employed in the Ni(0)-catalyzed isomerization of 2-methyl-3-butenenitrile (2M3BN), one of the key steps of industrial adiponitrile production by the DuPont process. The reaction showed a surprising preference for ligands bearing electron-donating substituents, such as methoxy or methyl groups, in the phenyl para position of the Ni-ligating PPh2 units. Octyltriptyphos (3) afforded the highest 2M3BN-isomerization turnover rate yet reported. A series of deuterium-labeling experiments was performed to investigate the possibility of an isomerization mechanism consisting of a cascade of de- and rehydrocyanation steps, which could be excluded. Using the ethano-bridged ligand 4, complex 16a (4-kappa P:kappa P')Ni(eta(3)-C4H7)CN (supposedly an intermediate of the 2M3BN-isomerization reaction) was isolated, and its solid-state structure was determined by X-ray diffraction analysis. The complete catalytic cycle of 2M3BN isomerization with ligand 4, as suggested by the available experimental evidence, was modeled using DFT methods.
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同类化合物

齐斯托醌 黄决明素 马普替林杂质E(N-甲基马普替林) 马普替林杂质D 马普替林 颜料黄199 颜料黄147 颜料黄123 颜料黄108 颜料红89 颜料红85 颜料红251 颜料红177 颜料紫27 顺式-1-(9-蒽基)-2-硝基乙烯 阿美蒽醌 阳离子蓝3RL 长蠕孢素 镁蒽四氢呋喃络合物 镁蒽 锈色洋地黄醌醇 锂钠2-[[4-[[3-[(4-氨基-9,10-二氧代-3-磺基-1-蒽基)氨基]-2,2-二甲基-丙基]氨基]-6-氯-1,3,5-三嗪-2-基]氨基]苯-1,4-二磺酸酯 锂胭脂红 链蠕孢素 铷离子载体I 铝洋红 铂(2+)二氯化1-({2-[(2-氨基乙基)氨基]乙基}氨基)蒽-9,10-二酮(1:1) 钾6,11-二氧代-6,11-二氢-1H-蒽并[1,2-d][1,2,3]三唑-4-磺酸酯 钠6,11-二氧代-6,11-二氢-1H-蒽并[1,2-d][1,2,3]三唑-4-磺酸酯 钠4-({4-[乙酰基(乙基)氨基]苯基}氨基)-1-氨基-9,10-二氧代-9,10-二氢-2-蒽磺酸酯 钠2-[(4-氨基-9,10-二氧代-3-磺基-9,10-二氢-1-蒽基)氨基]-4-{[2-(磺基氧基)乙基]磺酰基}苯甲酸酯 钠1-氨基-9,10-二氢-4-[[4-(1,1-二甲基乙基)-2-甲基苯基]氨基]-9,10-二氧代蒽-2-磺酸盐 钠1-氨基-4-[(3-{[(4-甲基苯基)磺酰基]氨基}苯基)氨基]-9,10-二氧代-9,10-二氢-2-蒽磺酸酯 钠1-氨基-4-[(3,4-二甲基苯基)氨基]-9,10-二氧代-9,10-二氢-2-蒽磺酸酯 钠1-氨基-4-(1,3-苯并噻唑-2-基硫基)-9,10-二氧代蒽-2-磺酸盐 醌茜隐色体 醌茜素 酸性蓝127:1 酸性紫48 酸性紫43 酸性兰62 酸性兰25 酸性兰182 酸性兰140 酸性兰138 酸性兰 129 透明蓝R 透明蓝AP 透明红FBL 透明紫BS