(+/-)-2-methylene-4-phenyl-1,4-butanediol | 5538-00-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-2-methylene-4-phenyl-1,4-butanediol
• 英文别名: 2-methylene-4-phenylbutane-1,4-diol；3-Methylene-1-phenylbutane-1,4-diol；2-methylene-4-phenyl-butane-1,4-diol；2-Methylen-4-phenyl-butan-1,4-diol；4-Phenyl-2-methylen-butandiol-(1,4)；3-Methylene-1-phenyl-1,4-butanediol；3-methylidene-1-phenylbutane-1,4-diol
• CAS: 5538-00-1
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: QRCPASPJZSIBLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-2-methylene-4-phenyl-1,4-butanediol 在 三氟甲磺酸三甲基硅酯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 4-(dimethoxymethyl)-2-phenyl-6-p-tolyltetrahydro-2H-pyran
  参考文献：
  名称：

  Diastereoselective Synthesis of 2,6-Disubstituted 4-(Dimethoxymethyl)tetra­hydropyrans Using TMSOTf-Promoted Prins-Pinacol Cyclization

  摘要：

  We have described a highly diastereoselective synthesis of 2,6-disubstituted 4-(dimethoxymethyl)tetrahydropyrans via TMSOTf-promoted Prins-pinacol reaction of methylene diol with acetals. This reaction provides an efficient procedure to synthesize functionalized tetrahydropyrans containing an acetal group at the C4 position with all-cis 2,4,6 relative configuration.

  DOI：

  10.1055/s-0033-1339709
• 作为产物：
  描述：

  3-苯甲酰基-2-亚甲基丙酸 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 (+/-)-2-methylene-4-phenyl-1,4-butanediol
  参考文献：
  名称：

  Quantitative Studies with Lithium Aluminum Hydride. The Reduction of Butenolides

  摘要：

  DOI：

  10.1021/ja01619a026

文献信息

• Palladium-catalysed carbonyl allylation by 2-methylenepropane-1,3-diol
  作者：Yoshiro Masuyama、Masaaki Kagawa、Yasuhiko Kurusu

  DOI：10.1039/cc9960001585

  日期：——

  2-Methylenepropane-1,3-diol first allylates an aldehyde exclusively at the allylic alcohol moiety at room temperature and then, at 50 °C, allylates another aldehyde also at the allylic alcohol moiety, in the presence of a catalytic amount of PdCl2(PhCN)2 with tin(II) chloride.

  2-甲烯基丙烷-1,3-二醇首先在室温下选择性地在烯丙醇部分对醛进行烯丙基化，然后在50°C下，在催化量的PdCl2(PhCN)2和氯化亚锡的存在下，再次在烯丙醇部分对另一个醛进行烯丙基化。
• 입체선택성 2,4,6-삼치환된 테트라하이드로파이란 유도체 및 이의 제조방법
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY 한국과학기술연구원(319980077518) BRN ▼209-82-03522

  公开号：KR101566829B1

  公开（公告）日：2015-11-06

  본 발명은 입체선택성 2,4,6-삼치환된 테트라하이드로파이란 유도체 및 이의 제조방법에 관한 것으로, 더욱 상세하게는 2-메틸렌-1,4-다이올 유도체를 출발물질로 하고 루이스산 촉매를 이용한 분자간 고리화 반응을 수행하여, C2, C4 및 C6 위치에 동시에 치환기가 도입된 입체선택성 2,4,6-삼치환된 테트라하이드로파이란 유도체 및 이의 제조방법에 관한 것이다.

  This invention relates to a chiral selective 2,4,6-trisubstituted tetrahydropyran derivative and its manufacturing method, more specifically, starting from a 2-methylene-1,4-diol derivative as a raw material and using a Lewis acid catalyst to perform an intramolecular cyclization reaction, introducing substituents at positions C2, C4, and C6 simultaneously to obtain the chiral selective 2,4,6-trisubstituted tetrahydropyran derivative and its manufacturing method.
• Tosylated lithium 2-(lithiomethyl)-2-propen-1-olate: a γ-alkoxide allyl sulfone anion in organic synthesis
  作者：Diego A. Alonso、Carmen Nájera、José M. Sansano

  DOI：10.1016/s0040-4020(01)89690-3

  日期：——

  Dilithiated 2-(tosylmethyl)-2-propen-1-ol (6) functioned as a nucleophile at the α-position of the allylic anion in reactions with deuterium oxide, alkyl halides, and aldehydes, and in conjugate additions to α,β-unsaturated carbonyl compounds. With nitro-olefins conjugate addition occurred at the γ-position of the allylic anion. The hydroxy ester derived by reaction with tert-butyl bromoacetate was

  在与氧化氘，烷基卤化物和醛的反应中，以及在与α，β的共轭加成反应中，二锂化的2-（甲苯磺酰基甲基）-2-丙烯-1-醇（6）在烯丙基阴离子的α位上起亲核试剂的作用。 -不饱和羰基化合物。对于硝基烯烃，共轭加成发生在烯丙基阴离子的γ-位。通过与溴乙酸叔丁酯反应得到的羟基酯被转化为各种合成上有用的二烯和β，γ-不饱和δ-内酯。还研究了一些羟基砜与钠汞齐的还原性脱甲苯基化作用。
• Boehme,H.; Haefner,L., Chemische Berichte, 1966, vol. 99, p. 879 - 884
  作者：Boehme,H.、Haefner,L.

  DOI：——

  日期：——
• Palladium-Catalyzed Carbonyl Allylation of Aldehydes by Allylic Cyclic Carbonates
  作者：Suk-Ku Kang、Dong-Chul Park、Chan-Hee Park、Su-Bum Jang

  DOI：10.1080/00397919508013837

  日期：1995.5

  Palladium(O)-catalyzed allylation of aldehydes by allylic cyclic carbonates with SnCl2 proceeded smoothly to afford 1,3-diols with high diastereocontrol. For the exomethylene cyclic carbonate, allylation with aldehydes furnished 1,4-diols or 1,5-diols depending on amount of aldehydes.