(1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-butyl-1,2-dihydronaphthalene | 99797-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-butyl-1,2-dihydronaphthalene
• 英文别名: (+)-trans-1-(hydroxymethyl)-2-n-butyl-1,2-dihydronaphthalene；(1R,2S)-(2-butyl-1,2-dihydronaphthyl)methan-1-ol；[(1R,2S)-2-butyl-1,2-dihydronaphthalen-1-yl]methanol
• CAS: 99797-47-4
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: SSHGZGRHFHVSAK-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-butyl-1,2-dihydronaphthalene 在 palladium on activated charcoal sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三乙醇胺 、 mercury(II) diacetate 、 氢气 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  A novel asymmetric synthesis of 3-benzyl-1,2,3,4,5,6-hexahydro-11-alkyl-2,6-methano-3-benzazocines

  摘要：

  9-烷基-6,7-苄莫沙芬（1,2,3,4,5,6-六氢-11-烷基-2,6-亚甲基-3-苄唑辛）是σ受体位点的重要选择性配体；以（1R, 2R）-或（1S, 2S）-1-羟甲基-2-烷基-2-烷基-1,2-二氢萘为起始原料的不对称合成方法已被描述。

  DOI：

  10.1039/c39940002401
• 作为产物：
  描述：

  α-naphtylidene-N-cyclohexylimine 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-butyl-1,2-dihydronaphthalene
  参考文献：
  名称：

  Design, Synthesis, and Application of a C₂ Symmetric Chiral Ligand for Enantioselective Conjugate Addition of Organolithium to α,β-Unsaturated Aldimine

  摘要：

  A C-2 symmetric chiral diether ligand, (1R,2R)-1,2-dimethoxy-1,2-diphenylethane was designed and synthesized on the basis of the concept of an asymmetric oxygen atom. Mediated by the chiral diether, high enantioselectivities were achieved in conjugate addition of organolithiums to naphthaldehyde imine and cyclic and acyclic alpha,beta-unsaturated aldimines. The absolute configuration of the product is predictable by the model.

  DOI：

  10.1021/jo9813181

文献信息

• Electronic and Steric Control in Regioselective Addition Reactions of Organolithium Reagents with Enaldimines
  作者：Kiyoshi Tomioka、Yoshito Shioya、Yasuo Nagaoka、Ken-ichi Yamada

  DOI：10.1021/jo015766b

  日期：2001.10.1

  A reaction mode of imines derived from naphthalene-1-carbaldehyde and acyclic alpha,beta-unsaturated aldehydes with organolitium reagents was dependent on the characteristic nature of a substituent on the imine nitrogen atom. An imine having an electron-withdrawing aryl group on the nitrogen atom behaves as a 1,2-directing imine toward organolithium reagents. In contrast, an imine bearing an alkyl

  衍生自萘-1-甲醛和无环α，β-不饱和醛的亚胺与有机锂试剂的反应方式取决于亚胺氮原子上取代基的特征。在氮原子上具有吸电子芳基的亚胺表现为朝向有机锂试剂的1,2-亚胺。相反，带有烷基或庞大的芳基的亚胺有利于有机锂试剂的1，4-加成。基于分子轨道计算，合理化了亚胺氮原子上取代基的电子和空间反应模式调节。
• A one-flask synthesis of dihydronaphthalenemethanols by directed addition of organolithium reagents to BHA naphthalenecarboxylates
  作者：Mitsuru Shindo、Kenji Koga、Yasutomi Asano、Kiyoshi Tomioka

  DOI：10.1016/s0040-4020(99)00181-7

  日期：1999.4

  The 1,4-addition reaction of organolithium reagents with 2,6-bis(tert-butyl)-4-methoxyphenyl naphthalenecarboxylates gave regioselectively substituted dihydronaphthalenecarboxylates in high yields. Successive treatment of the esters with organolithiums in THF, lithium triethylborohydride, methyl iodide, and finally sodium borohydride in methanol, provided regio- and stereoselectively the corresponding

  有机锂试剂与2，6-双（叔丁基）-4-甲氧基苯基萘羧酸酯的1，4-加成反应以高产率得到区域选择性取代的二氢萘羧酸酯。用四氢呋喃中的有机锂，三乙基硼氢化锂，甲基碘和最后用甲醇中的硼氢化钠连续处理酯类，可以很好地在区域和立体选择性地提供相应的1,1,2-和1,2,2-三取代的二氢萘基甲醇。该一烧瓶​​法由五个反应序列构成，该五个反应涉及作为关键步骤从烯酮还原性生成醛金属烯醇化物。
• Asymmetric additions to chiral naphthalenes. III. The synthesis of (+)-trans-1,2-disubstituted-1,2-dihydronaphthalenes
  作者：A. I. Meyers、Bruce A. Barner

  DOI：10.1021/jo00351a034

  日期：1986.1
• 1,2- vs. 1,4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines
  作者：Lendon N. Pridgen、Mohamed K. Mokhallalati、Ming Jung Wu

  DOI：10.1021/jo00030a035

  日期：1992.2

  We herein report our results where the addition of organomagnesium reagents to 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines occurred consistently in a 1,4-conjugate manner, while lithium, cerium, and copper organometallic reagents added in a 1,2-fashion. The 1,4-conjugate addition pathway was primarily exploited by using (4R)-2-(1-naphthyl)-4-phenyl-1,3-oxazolidine (4) as a substrate to obtain, after NaBH4 reduction of the intermediate aldehyde, trans-disubstituted 1,2-dihydronaphthalenes with enantiomeric excesses of 93-94%. The amino alcohol products resulting from 1,2-addition were oxidatively cleaved to afford enantiomeric enriched (R)-alpha-(1-naphthyl)alkylamines 6a and 6b in > 99% ee.
• Reductive generation of aldehyde metal enolate from ketene. A one-flask process to 1,1,2- and 1,2,2-trisubstituted dihydronaphthalenes from 1- and 2-naphthalenecarboxylates
  作者：Kiyoshi Tomioka、Mitsuru Shindo、Kenji Koga

  DOI：10.1021/jo00295a005

  日期：1990.4