(1R,2S)-2-乙炔基环庚烷-1-醇 | 25127-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2S)-2-乙炔基环庚烷-1-醇
• 英文名称: trans-2-Ethinylcycloheptanol
• 英文别名: trans-2-ethynylcycloheptanol；(1R,2S)-2-ethynylcycloheptan-1-ol
• CAS: 25127-83-7；61967-62-2；79894-69-2
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: XHVALGTUZARLIW-RKDXNWHRSA-N

物化性质

• 沸点：
  72 °C(Press: 3.5 Torr)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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)-2-乙炔基环庚烷-1-醇 在 sodium 2,2,2-trifluoroacetate 、 sodium carbonate 作用下， 以 二氯甲烷 、 三氟乙酸 为溶剂， 反应 168.0h， 生成 1-(环庚烯-1-基)乙酮
  参考文献：
  名称：

  Hanack, Michael; Schuhmacher, Werner; Kunzmann, Erich, Chemische Berichte, 1982, vol. 115, # 4, p. 1467 - 1487

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-环氧基环庚烷 、 乙炔氢锂 生成 (1R,2S)-2-乙炔基环庚烷-1-醇
  参考文献：
  名称：

  2-乙炔基环庚酮的光解：具有环扩展的光化学乙炔-丙二烯重排

  摘要：

  辐照2-乙炔基环庚酮可得到不寻常的烯丙基酮2,3-环壬二烯酮，作为主要的光化学产物。

  DOI：

  10.1039/c29690000674

文献信息

• Photolysis of 2-ethynylcycloheptanone: a photochemical acetylene–allene rearrangement with ring expansion
  作者：Robert G. Carlson、David E. Henton

  DOI：10.1039/c29690000674

  日期：——

  Irradiation of 2-ethynylcycloheptanone gives the unusual allenic ketone, 2,3-cyclononadienone, as the major photochemical product.

  辐照2-乙炔基环庚酮可得到不寻常的烯丙基酮2,3-环壬二烯酮，作为主要的光化学产物。
• Gold(I)-Catalyzed Access to Tetrahydropyran-4-ones from 4-(Alkoxyalkyl)oxy-1-butynes: Formal Catalytic Petasis-Ferrier Rearrangement
  作者：Hyo Jin Bae、Wook Jeong、Ji Hyung Lee、Young Ho Rhee

  DOI：10.1002/chem.201002918

  日期：2011.2.1

  Gold cycle redesigned: By utilizing the alkynophilic effect of gold(I) complexes, a new method for the synthesis of highly substituted cis‐2,6‐tetrahydropyranones was developed, which represents a catalytic surrogate of the Petasis–Ferrier rearrangement (see scheme). Of particular interest is the unique effect the phosphine ligand has on the diastereoselectivity of the alkyl groups at the 2‐ and 6‐positions

  重新设计了金的循环：通过利用金（I）配合物的嗜酸作用，开发了一种合成高度取代的顺式-2,6-四氢吡喃酮的新方法，该方法代表了Petasis-Ferrier重排的催化替代物（参见方案） 。特别令人感兴趣的是膦配体对2位和6位烷基的非对映选择性具有独特的作用。
• Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates
  作者：Mario D. Bachi、Eric Bosch

  DOI：10.1021/jo00043a030

  日期：1992.8

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.
• Palladium-catalyzed cyclocarbonylation of acetylenic alcohols to methylene lactones. Scope and synthesis of appropriate substrates
  作者：Timothy F. Murray、Edward G. Samsel、Vijaya Varma、Jack R. Norton

  DOI：10.1021/ja00415a020

  日期：1981.12
• Ruthenium-Catalyzed Cycloisomerization−Oxidation of Homopropargyl Alcohols. A New Access to γ-Butyrolactones
  作者：Barry M. Trost、Young H. Rhee

  DOI：10.1021/ja992013m

  日期：1999.12.1

  Vinylidenemetal species, which readily form from terminal alkynes under mild conditions, have rarely been utilized as reactive intermediates in a catalytic cycle. The conversion of homopropargyl alcohols via such intermediates to metal-complexed oxacarbenes led to the development of an "oxidant" compatible with a ruthenium complex capable of performing the cycloisomerization, that would convert them to lactones. None of the oxidants known to stoichiometrically convert isolated metallooxacarbenes to esters are effective. The unconventional "oxidants", N-hydroxyimides, proved to be capable of effecting the desired transformation, with N-hydroxysuccinimide being the "oxidant" of choice. The procedure of choice employs cyclopentadienyl (1,4-cyclooctadiene) ruthenium chloride and trifuryl phosphine as the precatalyst in the presence of tetra-n-butylammonium bromide or hexafluorophosphate with N-hydroxysuccinimide as the oxidant in DMF-water at 95 degrees. In this way, a wide diversity of homopropargyl alcohols were converted to gamma-butyrolactones with excellent chemoselectivity. Lactones synthesized include an intermediate toward a platelet aggregation inhibitor, a fruit flavor principle, an inhibitor of binding of phorbol esters to PKC-alpha, a tobacco constituent, a wood constituent (quercus lactone), an aldosterone antagonist (spironolactone) precursor, and an acetogenin known for pesticidal and antitumor activities (muricatacin).