trans-2-(ethoxy)cyclopentanol | 15051-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-2-(ethoxy)cyclopentanol
• 英文别名: (1R,2R)-2-ethoxycyclopentan-1-ol
• CAS: 15051-94-2
• 化学式: C₇H₁₄O₂
• mdl: MFCD28139436
• 分子量: 130.187
• InChiKey: CLFRTEKMZDRKMW-RNFRBKRXSA-N

物化性质

• 沸点：
  196.2±8.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H-吡唑-4-甲醛 、 trans-2-(ethoxy)cyclopentanol 在 四丁基高氯酸铵 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 生成 1-(6-ethoxytetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde 、 1-(6-ethoxytetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  无应变环烷醇的电化学解构和扩环官能化

  摘要：

  报道了一种从烷醇合成环醚和无环醛的有效且可持续的电化学方法。该策略已成功应用于具有不同环尺寸和不同类型亲核试剂的环烷醇。此外，机理研究表明反应经历连续过程，包括阳极氧化、β-断裂和亲核加成。该方法为从环烷醇和亲核试剂构建环醚和末端醛提供了一种新的合成方法。

  DOI：

  10.1021/acs.orglett.4c01337
• 作为产物：
  描述：

  3-ethoxycyclopentene 生成 trans-2-(ethoxy)cyclopentanol
  参考文献：
  名称：

  Hydroboration. XXVIII. The hydroboration of 3-cyclopentenyl derivatives containing representative substituents. Directive effects and the elimination reaction in a cyclic system

  摘要：

  DOI：

  10.1021/ja01018a042

文献信息

• Chiral synthesis via organoboranes. 45. Asymmetric hydroboration of 1-cyclopentenol derivatives using diisopinocampheylborane. Synthesis of optically active cyclopentane-1,2-diol derivatives of high optical purity
  作者：Herbert C. Brown、Dhanabalan Murali、Bakthan Singaram

  DOI：10.1016/s0022-328x(99)00047-9

  日期：1999.6

  The asymmetric hydroboration of 1-cyclopentenol derivatives, such as ethers, acetate, silyl ether and borinate, was investigated using diisopinocampheylborane, dIpc2BH. The product trialkylboranes were treated with excess of acetaldehyde to give the corresponding diethyl boronate esters. These boronate esters on oxidation using alkaline hydrogen peroxide gave optically active trans-cyclopentane-1,2-diol

  使用diisopinocampheylborane，d Ipc 2 BH研究了1-环戊烯醇衍生物（如醚，乙酸酯，甲硅烷基醚和硼酸酯）的不对称硼氢化。用过量的乙醛处理产物三烷基硼烷，得到相应的硼酸二乙酯。这些硼酸酯在使用碱性过氧化氢氧化后，以50-85％的对映体过量和高达95％的总收率得到了旋光性的反式-环戊烷-1,2-二醇衍生物。通过醚裂解将一些旋光的反式-2-烷氧基环戊醇转化为旋光的反式-（1 R，2 R）-环戊烷-1,2-二醇。3-甲氧基-2，5-二氢呋喃的不对称硼氢化反应以总产率的70％得到75％ee的反式-（3R，4R）-4-甲氧基四氢呋喃-3-醇。
• Highly Efficient, Regio- and Stereoselective Ring Opening of Epoxides and Thiiranes with Ce(OTf)₄
  作者：N. Iranpoor、M. Shekarriz、F. Shiriny

  DOI：10.1080/00397919808005728

  日期：1998.1

  Abstract Ceric triflate, Ce(OTf)4 is used as an efficient catalyst for ring opening of epoxides in the presence of alcohols, water, and acetic acid. The reactions proceed with high regio and stereoselectivity and in excellent yields. The reaction of R(+) styrene oxide with methanol occurs with excellent optical purity. Ring opening of thiiranes in alcohols, water and acetic acid followed by dimerisation

  摘要 三氟甲磺酸铈，Ce(OTf)4 被用作在醇、水和乙酸存在下环氧化物开环的有效催化剂。该反应以高区域选择性和立体选择性以及优异的产率进行。R(+) 氧化苯乙烯与甲醇的反应具有极好的光学纯度。在这种试剂的存在下，硫杂丙环在醇、水和乙酸中开环，然后二聚成相应的二硫化物。还描述了一种从硫杂丙烷和 Ce(OTf)4 制备二噻烷的温和方法。
• Mild regiospecific alcoholysis and aminolysis of epoxides catalyzed by zirconium(IV) oxynitrate
  作者：Sandip S. Shinde、Madhukar S. Said、Trupti B. Surwase、Pradeep Kumar

  DOI：10.1016/j.tetlet.2015.09.031

  日期：2015.10

  A regiospecific method for the ring-opening reaction of epoxides by the primary, secondary, tertiary alcohols, and aryl, aliphatic amines has been developed using non-toxic metal nitrate salt as a catalyst. The best results were obtained using zirconium(IV) oxynitrate among the various screened metal nitrate salts. The reported protocol works efficiently for styrene epoxide and aliphatic as well.

  已经开发出使用无毒金属硝酸盐作为催化剂的伯，仲，叔醇和芳基，脂族胺通过环氧化物开环反应的区域特异性方法。在各种经筛选的金属硝酸盐中，使用硝酸氧锆（IV）可获得最佳结果。报告的协议对苯乙烯环氧化物和脂肪族化合物也有效。
• Iron(III) Trifluoroacetate as an Efficient Catalyst for Solvolytic and Nonsolvolytic Nucleophilic Ring Opening of Epoxides
  作者：Nasser Iranpoor、Hadi Adibi

  DOI：10.1246/bcsj.73.675

  日期：2000.3

  Iron(III) trifluoroacetate was used as an efficient and nonhygroscopic catalyst for the alcoholysis, hydrolysis, and acetolysis of epoxides. The addition of chloride, bromide, iodide, and nitrate ions to epoxides to produce the corresponding 2-halo and 2-nitratoalkanols and also the conversion of epoxides to acetonides and thiiranes were also performed efficiently in the presence of this catalyst.

  三氟乙酸铁（III）被用作一种高效且不吸湿的催化剂，用于环氧化物的醇解、水解和乙酰分解。在该催化剂的作用下，氯离子、溴离子、碘离子和硝酸根离子与环氧化物的加成反应可生成相应的 2-卤代烷醇和 2-硝基烷醇，环氧化物与丙酮和硫代烷烃的转化反应也可高效进行。
• A novel mononuclear Fe(iii) mono(terpyridine) complex having labile solvent ligands and its catalytic activityElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/dt/b2/b208413a/
  作者：Dong-Woo Yoo、Sang-Kun Yoo、Cheal Kim、Jin-Kyu Lee

  DOI：10.1039/b208413a

  日期：2002.10.29

  A novel Fe mono(terpyridine) complex was successfully prepared by deliberately choosing the polymer surface-anchored terpyridine as a chelating ligand and it showed an excellent catalytic activity with an easy reusability on the ring-opening reaction of various epoxides by alcohol and water under mild and neutral conditions to give stereospecific and regioselective products.

  通过特意选择聚合物表面锚定的萜吡啶作为螯合配体，成功制备了一种新型铁单（萜吡啶）配合物，该配合物在温和的中性条件下，对各种环氧化物与醇和水的开环反应具有极佳的催化活性，且易于重复使用，可得到立体选择性和区域选择性产物。