(R)-(+)-cyclohex-3-ene-1-methanol | 5709-99-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-cyclohex-3-ene-1-methanol
• 英文别名: (R)-4-(Hydroxymethyl)cyclohexene；(R)-1-(3-Cyclohexenyl)methanol；(R)-1-C-(1-Cyclohexen-5-yl)methanol；(1R)-cyclohex-3-enemethanol；(-)-(S)-Cyclohexen-(3)-methanol-(1)；(R)-(cyclohex-3-en-1-yl)methanol；(R)-4-Hydroxymethyl-cyclohexen；(R)-3-cyclohexene-1-methanol；4-(hydroxymethyl)cyclohexene；(+)-3-Cyclohexenyl-1-methanol；(R)-3-Cyclohexen-1-methanol；3-Cyclohexene-1-methanol, (R)-；[(1R)-cyclohex-3-en-1-yl]methanol
• CAS: 5709-99-9
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: VEIYJWQZNGASMA-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (R)-(+)-cyclohex-3-ene-1-methanol 在 silver carbonate 作用下， 生成 (R)-1-C-(1-Cyclohexen-5-yl)carbaldehyde
  参考文献：
  名称：

  Ceder,O.; Nilsson,H.G., Synthetic Communications, 1976, vol. 6, p. 381 - 386

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-(+)-methyl 3-cyclohexene-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以99%的产率得到(R)-(+)-cyclohex-3-ene-1-methanol
  参考文献：
  名称：

  摘要：

  Cyclic nucreo-delta-amino acids that constitute monomers of a conformationally constrained nucleo-delta-peptide base-pairing system have been prepared. Their synthesis starts with an enantioselectively catalyzed chirogenic Diels-Alder reaction, proceeds via a regioselective epsilon-iodolactamization process, and ends with a regio- as well as diastereoselective introduction of nucleobases through S(N)2-type opening of a transiently formed N-acylaziridine ring. Extensive use of X-ray crystal-structure analysis has been made to support structure assignments.

  DOI：

  10.1002/1522-2675(20000607)83:6<1049::aid-hlca1049>3.0.co;2-1

文献信息

• Mechanism of a Diels-Alder reaction. Butadiene and its dimers
  作者：W. von E. Doering、M. Franck-Neumann、D. Hasselmann、R. L. Kaye

  DOI：10.1021/ja00766a029

  日期：1972.5

  the trans,trans (or, less probably, the cis,cis) diradical to butadiene to be 81.1 5 2.0 kcal/mol, in good agreement with that (82.3 kcal/mol) deduced for the same reaction in the transformations of trans-divinylcyclobutane investigated by Hammond and DeBoer. In relation to the transition state for the Diels-Alder reaction of butadiene with itself to give Cvinylcyclohexene, the cleavage of the diradical

  (I?)-(+)-1 ,l-dideuterio-2-(cyclohex-3-enyl)ethene（标记为 4vinylcyclohexene）的合成和动力学研究揭示了外消旋化和氘交换的新反应，前者固定了顺式，反式（和/或顺式，顺式）八-3,6-二烯-1,7-二基双自由基的形成热比以往更牢固。重新确定环辛基-1,5-二烯热反应的动力学参数确定反式、反式（或不太可能的顺式、顺式）双自由基裂解为丁二烯的形成热为 81.1 5 2.0 kcal /mol，与由 Hammond 和 DeBoer 研究的反式二乙烯基环丁烷转化中相同反应推导出的 (82.3 kcal/mol) 非常一致。关于丁二烯与其自身进行 Diels-Alder 反应生成 C乙烯基环己烯的过渡态，在目前的实验结果限制范围内，双自由基的裂解似乎能量稍高。这种 Diels-Alder 反应的机制暂时被认为是协调一致的，可能是两阶段，但不是两步。关于
• AsymmetricDiels-Alder Reactions of Neopentyl-Ether-Shielded Acrylates and Allenic Esters: Syntheses of (?)-Norbornenone and (?)-?-Santalene
  作者：Wolfgang Oppolzer、Christian Chapuis、Dominique Dupuis、Maodao Guo

  DOI：10.1002/hlca.19850680803

  日期：1985.12.18

  Starting from (+)- or (−)-camphor, the antipodal alcohols 14 and 18, respectively, have been prepared; the corresponding acrylates 15 and 19 underwent TiCl2(i-PrO)2-mediated Diels-Alder additions to cyclopentadiene to give adducts 20a and 22a respectively, with 95 % endo- and 99.2% πpH-face selectivities. Adduct 22a was converted to enantiomerically pure norbornenone 26. Addition of 1,3-butadiene to

  从（+）-或（-）-樟脑开始，分别制备了对映体醇14和18。相应的丙烯酸酯15和19经历TiCl 2（i-PrO）2介导的Diels - Alder加成到环戊二烯中，分别得到加合物20a和22a，其内表面选择性和95 ％πpH选择性。加合物22a被转化为对映体纯的降冰片烯酮26。在TiCl 4存在下将1,3-丁二烯添加到丙烯酸酯15中得到具有＞ 95.6％的立体分化的3-环己烯基羧酸盐29。TiCl 2（i-PrO）2促进的环戊二烯与烯丙基酯43的[4 + 2]环加成反应，并进行了99％的表面分化，是有效（-）-β-檀香烯（（- ）-41）同时回收手性对照醇14。
• Bicyclo-octane and bicyclo-nonane derivatives, processes for their preparation and their use as herbicides
  申请人：HER MAJESTY THE QUEEN IN RIGHT OF NEW ZEALAND, DEPARTMENT OF SCIENTIFIC AND INDUSTRIAL RESEARCH, CHEMISTRY DIVISON

  公开号：EP0302599A2

  公开（公告）日：1989-02-08

  Bicyclo-octane and bicyclo-nonane derivatives are described having herbicidal and plant growth regulating properties. The derivatives are based on the general formula

  双环辛烷和双环壬烷衍生物具有除草和植物生长调节性能。这些衍生物基于一般公式。
• [EN] NOVEL COMPOUNDS AND METHODS FOR INCREASING KLOTHO GENE EXPRESSION<br/>[FR] NOUVEAUX COMPOSÉS ET MÉTHODES PERMETTANT D'AUGMENTER L'EXPRESSION DU GÈNE KLOTHO
  申请人：KLOTHO THERAPEUTICS INC

  公开号：WO2022011171A1

  公开（公告）日：2022-01-13

  Novel compounds and compositions including the same and methods of manufacturing and using the same, particularly for increasing klotho gene expression, and more particularly for increasing circulating or soluble Klotho protein levels through increasing klotho gene expression.

  包括新化合物和组合物以及制造和使用这些化合物的方法，特别是用于增加克洛托基因表达，更具体地通过增加克洛托基因表达来增加循环或可溶性克洛托蛋白水平的小说化合物和组合物。
• Practical AsymmetricDiels-Alder Additions to Camphor-10-sulfonic-Acid-Derived Acrylates. Preliminary Communication
  作者：Wolfgang Oppolzer、Christian Chapuis、Martha J. Kelly

  DOI：10.1002/hlca.19830660747

  日期：1983.11.2

  Starting from (+)-camphor-10-sulfonic acid (1) the chiral crystalline alcohols 3 and 11 were prepared in two steps. Lewis-acid-mediated [4+2]-additions of their acrylates to 1,3-dienes were studied. Notably, the crystalline acrylate 4 underwent TiCl2 (OiPr)2-promoted Diels-Alder addition to cyclopentadiene giving after recrystallization efficiently the pure (2R)-adduct 5.

  从（+）-樟脑-10-磺酸（1）开始，分两步制备手性结晶醇3和11。研究了路易斯酸介导的丙烯酸酯向[1,3-二烯]的[4 + 2]加成反应。值得注意的是，在重结晶后，结晶的丙烯酸酯4经受了环戊二烯的TiCl 2（OiPr）2促进的Diels - Alder加成，从而有效地提供了纯的（2 R）加合物5。