3-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionitrile | 7647-30-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionitrile
• 英文别名: 3-(1-oxo-3,4-dihydro-2H-naphthalen-2-yl)propanenitrile
• CAS: 7647-30-5
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: XOALNZJYVSUGOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionitrile 在 四乙基对甲苯磺酸铵 作用下， 以 异丙醇 为溶剂， 以60%的产率得到2-(2-cyanoethyl)-1-tetralol
  参考文献：
  名称：

  Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.

  摘要：

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.

  DOI：

  10.1021/jo00052a036
• 作为产物：
  描述：

  3,4-二氢-1(2H)-萘酮 生成 3-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionitrile
  参考文献：
  名称：

  CHATTERJEA, J. N.;OJHA, N., NAT. ACAD. SCI. LETT., 11,(1989) N0, C. 311-312

  摘要：

  DOI：

文献信息

• Cp2TiPh-coordinated cyano and ester groups as efficient ketyl radical acceptors in the reductive radical cyclization of γ- and δ-cyano ketones and δ-keto esters
  作者：Yoshihiko Yamamoto、Daisuke Matsumi

  DOI：10.1039/a800661j

  日期：——

  Cp2TiPh promotes the reductive radical cyclization of γ- and δ-cyano ketones and δ-keto esters to give α-hydroxycycloalkanones in moderate to good yields; the titanium reagent coordinates to both the ketone and the cyano or ester terminus, the LUMO of the cyano or ester group is thus lowered, and cyclization proceeds irreversibly without formation of the unstable iminyl or alkoxy radical intermediates.

  Cp2TiPh促进了γ-和δ-氰基酮及δ-酮酯的还原自由基环化，得到α-羟基环状酮，产率适中到良好；钛试剂与酮和氰基或酯末端均形成配位，氰基或酯基团的LUMO因此降低，环化过程不可逆进行，不会形成不稳定的亚胺或烷氧自由基中间体。
• Reductive radical cyclization of cyclic γ-cyanoketones promoted by samarium(II) iodide without photoirradiation
  作者：Kiyomi Kakiuchi、Yasunari Fujioka、Hirohisa Yamamura、Ken Tsutsumi、Tsumoru Morimoto、Hideo Kurosawa

  DOI：10.1016/s0040-4039(01)01579-9

  日期：2001.10

  Reaction of cyclic γ-cyanoketones with 3 equiv. of SmI2 in the presence of t-BuOH as a proton source in HMPA–THF without photoirradiation gave the desired α-hydroxycycloalkanones along with overreduced ketones after hydrolysis. In the absence of t-BuOH, the formation of the overreduced ketones was depressed and the yields of the α-hydroxyketones increased, while the reaction proceeded slowly.

  环状γ-氰基酮与3当量的反应 在没有光辐照的情况下，在没有光辐照的情况下，在叔丁醇存在下，在叔丁醇中作为质子源的SmI 2产生了所需的α-羟基环烷酮以及水解后的过度还原的酮。在不存在t- BuOH的情况下，抑制了过度还原的酮的形成，并且增加了α-羟基酮的产率，同时反应进行缓慢。
• DBU Promoted Deformylative/Dehalogenative Difunctionalization to Access β‐Bromovinyl Aldehydes Derived from Tetralones**
  作者：Madan Sau、Sapana Dubey、Shreya Roy、Shubhankar Samanta、Tapas Das

  DOI：10.1002/ejoc.202300788

  日期：——

  Metal-free deformylative/dehalogenative carbonylation, Michael addition of β-bromovinyl aldehydes for the synthesis of δ-oxo esters and vinyl ethers have been reported. Nucleophilic and organo-catalytic behaviour of DBU is explored and the regeneration of the parent starting material from the vinyl ether is also highlighted.

  已经报道了无金属脱酰基/脱卤羰基化、β-溴乙烯基醛的迈克尔加成用于合成 δ-氧代酯和乙烯基醚。探索了 DBU 的亲核和有机催化行为，并重点介绍了乙烯基醚母体原料的再生。
• Ring enlargements. XI. Structural influences on the course of the intramolecular diazo alkane-carbonyl reaction
  作者：C. David Gutsche、John E. Bowers

  DOI：10.1021/jo01279a078

  日期：1967.4
• The Cp₂TiPh-Mediated Reductive Radical Cyclization of Cyanoketones and Related Reactions. Efficient Trapping of Ketyl Radicals by Cp₂TiPh-Coordinated Polar Multiple Bonds
  作者：Yoshihiko Yamamoto、Daisuke Matsumi、Reiko Hattori、Kenji Itoh

  DOI：10.1021/jo982492s

  日期：1999.4.1

  The reductive radical cyclization of cyanoketones was achieved using Cp2TiPh. The Ti(III) reagent was prepared by the sequential addition of i-PrMgCl and PhMgBr to commercial Cp2TiCl2 in this order and used effectively without isolation. The cyclization of the gamma- and delta-cyanoketones was performed in toluene at ambient temperature for several hours to give alpha-hydroxycyclopentanones and hexanones in moderate to good yields, respectively. The titanium reagent independently coordinates to both the carbonyl and cyano termini. As a result of lowering the LUMO of the cyano group upon coordination of the Ti(III) species, the irreversible cyclization successfully proceeds without formation of the unstable iminyl radical intermediate. The ester group can also be activated by the coordination of Cp2TiPh, and aromatic ketones with an ester group at the gamma position are cyclized to give the corresponding alpha-hydroxyketones.