1-((Z)-styryl)adamantine | 70624-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-((Z)-styryl)adamantine
• 英文别名: (Z)-(3r,5r,7r)-1-(styryl)adamantine；(3r,5r,7r)-1-(styryl)adamantane；(3r,5r,7r)-1-((Z)-styryl)adamantane；1-(1-adamantyl)-2-phenylethene；1-[(Z)-2-phenylethenyl]adamantane
• CAS: 70624-81-6
• 化学式: C₁₈H₂₂
• 分子量: 238.373
• InChiKey: PSNFGYKRQUZKPQ-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 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-金刚烷甲醛 、 苯基次甲基三苯基膦烷 、 1-((Z)-styryl)adamantine 以42%的产率得到
  参考文献：
  名称：

  SASAKI TADASHI; USUKI ARIMITSU; OHUO MASATOMI, TETRAHEDRON LETT., 1978, NO 49, 4925-4928

  摘要：

  DOI：
• 作为产物：
  描述：

  Z-2-adamantyl-1-chloro-1-phenylethene 生成 1-((Z)-styryl)adamantine
  参考文献：
  名称：

  SASAKI TADASHI; USUKI ARIMITSU; OHUO MASATOMI, TETRAHEDRON LETT., 1978, NO 49, 4925-4928

  摘要：

  DOI：

文献信息

• Selective Syntheses of <i>Z</i>-Alkenes via Photocatalyzed Decarboxylative Coupling of <i>N</i>-Hydroxyphthalimide Esters with Terminal Arylalkynes
  作者：Guo-Li Dai、Shu-Zhen Lai、Zhuangzhu Luo、Zhen-Yu Tang

  DOI：10.1021/acs.orglett.9b00558

  日期：2019.4.5

  A novel, efficient Z-alkene synthesis via photocatalyzed decarboxylative couplings between terminal aryl alkynes and alkyl N-hydroxyphthalimide (NHPI) esters, which are derived from aliphatic carboxylic acids, is described. A wide range of primary, secondary, and tertiary carboxylates as well as α-amino acid and α-oxyacid-derived esters were employed as suitable substrates. The mild reaction conditions

  描述了通过末端芳基炔烃和衍生自脂族羧酸的烷基N-羟基邻苯二甲酰亚胺（NHPI）酯之间的光催化脱羧偶联的新颖，有效的Z-烯烃合成。各种各样的伯，仲和叔羧酸盐以及α-氨基酸和α-含氧酸衍生的酯被用作合适的底物。温和的反应条件，广泛的底物范围，官能团耐受性和操作简便性使得该脱羧偶联反应成为有机合成中的重要方法。
• <i>Cis</i>-Selective Decarboxylative Alkenylation of Aliphatic Carboxylic Acids with Vinyl Arenes Enabled by Photoredox/Palladium/Uphill Triple Catalysis
  作者：Chao Zheng、Wan-Min Cheng、Hong-Lian Li、Ri-Song Na、Rui Shang

  DOI：10.1021/acs.orglett.8b00712

  日期：2018.5.4

  An iridium photoredox catalyst in combination with phenanthroline-supported palladium catalyst catalyzes decarboxylative alkenylation of tertiary and secondary aliphatic carboxylic acids with vinyl arenes to deliver β-alkylated styrenes with Z-selectivity. A broad scope of aliphatic carboxylic acids, including amino acids, exhibit as amenable substrates, and external oxidant is not required. The reaction

  铱光氧化还原催化剂与菲咯啉负载的钯催化剂的组合催化叔和仲脂族羧酸与乙烯基芳烃的脱羧烯基化反应，以Z选择性输送β-烷基化苯乙烯。各种各样的脂族羧酸，包括氨基酸，表现出可作为合适的底物，并且不需要外部氧化剂。通过协同利用铱光氧化还原催化剂的能量转移和电子转移反应性与钯催化的氢化物消除和插入反应来进行反应。
• Silver-Catalyzed Regioselective Carbomagnesiation of Alkynes with Alkyl Halides and Grignard Reagents
  作者：Nobuaki Kambe、Yuusuke Moriwaki、Yuuki Fujii、Takanori Iwasaki、Jun Terao

  DOI：10.1021/ol2018664

  日期：2011.9.2

  A silver-catalyzed carbomagnesiation of alkynes with alkyl halides and Grignard reagents afforded alkenyl Grignard reagents regioselectively, where the alkyl group of the alkyl halide, but not that of the Grignard reagent, was introduced into the alkyne. Application to δ-haloalkylacetylenes yielded cyclopentanes or a tetrahydrofuran containing an exo-methylene substituent via 5-exo-dig cyclization

  银的炔烃与烷基卤化物和格利雅试剂的银催化碳还原反应可选择性地提供烯基格利雅试剂，其中烷基卤的烷基而不是格利雅试剂的烷基被引入炔中。到δ-haloalkylacetylenes得到应用环戊烷或含四氢呋喃外型亚甲基取代基经由5外切挖环化。
• Rhodium‐Catalyzed Regio‐ and Diastereoselective [3+2] Cycloaddition of <i>gem</i>‐Difluorinated Cyclopropanes with Internal Olefins
  作者：Yaxin Zeng、Ying Xia

  DOI：10.1002/anie.202307129

  日期：2023.8.7

  A rhodium-catalyzed [3+2] cycloaddition reaction between readily available gem-difluorinated cyclopropanes and internal olefins has been developed, providing a wide range of multisubstituted gem-difluorinated cyclopentanes. This reaction shows an example where the “CF2” motif can be kept upon ring extension. The process is atom-economic and allows to reach numerous gem-difluorinated cyclopentanes with

  已经开发了易于获得的偕二氟化环丙烷和内烯烃之间的铑催化[3+2]环加成反应，提供了多种多取代偕二氟化环戊烷。该反应显示了“CF 2 ”基序可以在环延伸时保留的例子。该方法是原子经济的，并且可以得到许多具有良好区域选择性和非对映选择性的偕二氟化环戊烷。
• An Organocatalytic System for Z-Alkene Synthesis via a Hydrogen-Bonding-Assisted Photoinduced Electron Donor–Acceptor Complex
  作者：Hui Zhao、Yingxiao Zong、Yue Sun、Guanghui An、Junke Wang

  DOI：10.1021/acs.orglett.4c00433

  日期：2024.3.1

  photoinduced electron donor–acceptor (EDA) complex and energy transfer was developed. This mild and metal-free protocol allows facile access to various Z-alkenes. Mechanism studies revealed that the organophotocatalyst, 4-CzIPN, formed a distinct three-component EDA complex with redox-active esters and (C6H5O)2P(O)OH to trigger the photoredox catalysis. The E → Z isomerization was achieved via electron exchange

  开发了一种用于光诱导电子供体-受体（EDA）复合物和能量转移组合的通用催化供体。这种温和且不含金属的方案可以轻松获得各种Z-烯烃。机理研究表明，有机光催化剂 4-CzIPN 与氧化还原活性酯和 (C 6 H 5 O) 2 P(O)OH 形成独特的三组分 EDA 复合物，以触发光氧化还原催化。 E → Z异构化是通过 4-CzIPN 的电子交换能量转移实现的。