4-methylchroman-4-ol | 21834-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-methylchroman-4-ol
• 英文别名: 4-methyl-2,3-dihydrochromen-4-ol
• CAS: 21834-65-1
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: RCMBJZYJTXAPFF-UHFFFAOYSA-N

物化性质

• 熔点：
  107 °C
• 沸点：
  287.6±29.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  4-methylchroman-4-ol 生成 4-methyl-2H-chromene
  参考文献：
  名称：

  Time-Resolved Absorption Studies on the Photochromic Process of 2H-Benzopyrans in the Picosecond to Submillisecond Time Domain

  摘要：

  Picosecond to submillisecond photochromic reactions of 2,4-diphenyl-2H-benzopyran and 2,2,4-triphenyl2H-benzopyran have been investigated by time-resolved absorption spectroscopy. The C-O bond cleavage of the benzopyrans (closed forms) occurs via the first excited singlet state within 2 ps to produce vibrationally excited open forms in the ground electronic state. In the subnanosecond to submillisecond time domain, several decay components with almost the same spectral profiles are observed. These components are assigned to respective stereoisomers with respect to two double bonds and one single bond of the open enone forms. From the pump-laser power dependencies of the yields of the open forms, it is suggested that the photocleavage gives at first only the open forms revertible to the closed form by a single-bond rotation, and that the photoexcitation of the first generated open forms gives rise to other open forms which need a double-bond rotation for reversion to the closed form. The photochromic reactions of a series of 2H-benzopyrans bearing substituents on the pyran ring have also been studied using nanosecond time-resolved absorption spectroscopy. The size of a substituent in the 4-position fairly affects the rate constants of the thermal reversion of the open form to the closed form.

  DOI：

  10.1021/jp002032e
• 作为产物：
  描述：

  2,3-二氢苯并吡喃-4-酮 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 以84%的产率得到4-methylchroman-4-ol
  参考文献：
  名称：

  通过苄基叔醇的氧化重排获得不同的氧杂环

  摘要：

  通过苄基叔醇的新型氧化重排，已开发出一种简便的合成具有挑战性的中型环状醚的方法。该反应提供了在C 2和芳环上具有不同取代基的环状缩醛的途径。独特的反应性是由聚（阳离子）高价碘试剂实现的，代表了该类化合物的未开发应用的首次合成应用。

  DOI：

  10.1021/acs.orglett.6b00672

文献信息

• From Cycloalkanols to Heterocycles via Nitrogen Insertion
  作者：Alexander Sandvoß、Johannes M. Wahl

  DOI：10.1021/acs.orglett.3c02048

  日期：2023.8.11

  transition-metal-free nitrogen insertion provides access to a variety of medicinally relevant heterocycles such as pyrrolidenes, quinolines, and benzazepines (24 examples). Furthermore, combination with a photochemical Norrish–Yang-type cyclization allows an unprecedented access to indoles from ortho-substituted acetophenones.

  发现多种环醇通过O-异三叉基磺酰基羟胺进行氮插入。成功过程的关键是使用氟化醇溶剂，这可确保充分的底物活化，以允许与两亲性胺化剂结合。这种无过渡金属的氮插入提供了获得各种医学相关杂环的途径，例如吡咯烷、喹啉和苯并氮杂环（24 个例子）。此外，与光化学诺里什-杨型环化相结合，可以前所未有地从邻位取代的苯乙酮中获得吲哚。
• Kinetic Resolution of Cyclic Tertiary Alcohols with Lipase A from Candida Antarctica
  作者：Satoshi Horino、Karla Wagner、Anke Hummel、Kyohei Kanomata、Harald Gröger、Shuji Akai

  DOI：10.1002/ejoc.202400242

  日期：2024.6.3

  with Na2CO3 is the key to substantially improving the reaction rate, substrate scope, and product stability in the KR of racemic tertiary alcohols using commercially available lipase A from Candida antarctica. The KR conditions were applied to cyclic tertiary alcohols containing tetralin, dihydroindene, chromane, and thiochromane moieties, yielding esters with excellent enantioselectivities.

  使用己酸乙烯酯作为 Na 2 CO 3 的酰基供体是使用市售的外消旋叔醇 KR 大幅提高反应速率、底物范围和产物稳定性的关键来自南极洲念珠菌的脂肪酶 A。 KR 条件适用于含有四氢化萘、二氢茚、苯并二氢吡喃和硫代苯并二氢吡喃部分的环状叔醇，产生具有优异对映选择性的酯。
• Arndt; Pusch, Chemische Berichte, 1925, vol. 58, p. 1647
  作者：Arndt、Pusch

  DOI：——

  日期：——